Minocycline

Last updated

Minocycline
Minocycline.svg
Minocycline (model).png
Clinical data
Trade names Minocin, Amzeeq, others
AHFS/Drugs.com Monograph
MedlinePlus a682101
License data
Pregnancy
category
Routes of
administration
By mouth, intravenous, topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 90–100% [4]
Protein binding 70–75% [5]
Metabolism Liver [5]
Elimination half-life 14–22 [5] (11–26 [4] ) hours
Excretion Mostly fecal, 10–15% renal [5]
Identifiers
  • (2E,4S,4aR,5aS,12aR)-2-(Amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6- tetrahydro-4H-tetracene-1,3,12-trione [6]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.226.626 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H27N3O7
Molar mass 457.483 g·mol−1
3D model (JSmol)
Specific rotation = −166° [5]
Solubility in water Low
  • CN(C)c1ccc(c2c1C[C@H]3C[C@H]4[C@@H](C(=C(C(=O)[C@]4(C(=C3C2=O)O)O)C(=O)N)O)N(C)C)O
  • InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1 Yes check.svgY
  • Key:DYKFCLLONBREIL-KVUCHLLUSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Minocycline, sold under the brand name Minocin among others, is a tetracycline antibiotic medication used to treat a number of bacterial infections such as some occurring in certain forms of pneumonia. [2] [4] [7] It is generally (but not always) less preferred than the tetracycline doxycycline. [4] [7] Minocycline is also used for the treatment of acne and rheumatoid arthritis. [7] [3] It is taken by mouth or applied to the skin. [4] [3]

Contents

Common side effects include nausea, diarrhea, dizziness, allergic reactions, and kidney problems. [4] Serious side effects may include anaphylaxis, a lupus-like syndrome, and easy sunburning. [4] Use in the later part of pregnancy may harm the baby and safety during breastfeeding is unclear. [8] It works by decreasing a bacterium's ability to make protein thus stopping its growth. [4]

Minocycline was patented in 1961 and came into commercial use in 1971. [9] It is available as a generic medication. [7] [10] In 2021, it was the 229th most commonly prescribed medication in the United States, with more than 1 million prescriptions. [11] [12]

Medical uses

Minocycline 100-mg capsules manufactured by Ranbaxy Pharmaceuticals Minocycline-150.jpg
Minocycline 100-mg capsules manufactured by Ranbaxy Pharmaceuticals

Acne

Minocycline is indicated to treat inflammatory lesions of non-nodular moderate to severe acne vulgaris in people nine years of age and older. [13] [3]

Minocycline and doxycycline are frequently used for the treatment of acne vulgaris. [14] [15] Both of these closely related antibiotics have similar levels of efficacy, although doxycycline has a slightly lower risk of adverse side effects. [16] Historically, minocycline has been an effective treatment for acne vulgaris. [17] However, acne that is caused by antibiotic-resistant bacteria is a growing problem in many countries. [18] In Europe and North America, a number of people with acne no longer respond well to treatment with tetracycline family antibiotics because their acne symptoms are caused by bacteria (primarily Cutibacterium acnes ) that are resistant to these antibiotics. In order to reduce resistance rates as well as increase the effectiveness of treatment, oral antibiotics should be generally combined with topical acne creams such as benzoyl peroxide or a retinoid (tretinoin, adapalene, etc.). [19]

Infections

Minocycline is also used for other skin infections such as methicillin-resistant Staphylococcus aureus. [20]

Although minocycline's broader spectrum of activity, compared with other members of the group, includes activity against Neisseria meningitidis , [21] its use for prophylaxis is no longer recommended because of side effects (dizziness and vertigo).

It may be used to treat certain strains of methicillin-resistant S. aureus infection and a disease caused by drug-resistant Acinetobacter spp. [22]

A list of uses includes:

Other

Both minocycline and doxycycline have shown effectiveness in asthma due to immune-suppressing effects. [26] Minocycline and doxycycline have modest effectiveness in treating rheumatoid arthritis. [27] However, the 2015 American College of Rheumatology guideline for the treatment of rheumatoid arthritis does not include minocycline. [28] Recent research indicate that centrally infused minocycline attenuates brain microglial activation, neuroinflammation and sympathetic activation during pulmonary hypertension. [29]

Contraindications

The drug is contraindicated in people with known hypersensitivity to tetracycline antibiotics, as there is complete cross sensitivity in this group. It is also contraindicated in people with severe liver impairment and after the 16th week of pregnancy. [5]

Side effects

Minocycline may cause upset stomach, diarrhea, dizziness, unsteadiness, drowsiness, mouth sores, migraines, and vomiting. It increases sensitivity to sunlight, and may affect the quality of sleep and rarely causes sleep disorders. [30] It has also been linked to cases of lupus. [31] Prolonged use of minocycline can lead to blue-gray staining of skin, fingernails, and scar tissue. This staining is not permanent, but can take a very long time for the skin color to return to normal; however, a muddy brown skin color in sun-exposed areas is usually permanent. [32] Permanent blue discoloration of gums or teeth discoloration may also occur. Rare but serious side effects include fever, yellowing of the eyes or skin, stomach pain, sore throat, vision changes, and mental changes, including depersonalization. [33] [34]

Occasionally, minocycline therapy may result in autoimmune disorders such as drug-related lupus and autoimmune hepatitis, which usually occurs in men who also developed minocycline-induced lupus; however, women are more likely to develop minocycline-induced lupus. Significant or complete recovery occurs in most people who develop minocycline-induced autoimmune problems within a period of a few weeks to a year of cessation of minocycline therapy. Autoimmune problems emerge during chronic therapy, but can sometimes occur after only short courses of a couple of weeks of therapy. [35] [36] Drug reaction with eosinophilia and systemic symptoms syndrome can occur during the first few weeks of therapy with minocycline. [36]

Minocycline, but not other tetracyclines, can cause vestibular disturbances with dizziness, ataxia, vertigo, and tinnitus. These effects are thought to be related to minocycline's greater penetration into the central nervous system. Vestibular side effects are much more common in women than in men, occurring in 50 to 70% of women receiving minocycline. As a result of the frequency of this bothersome side effect, minocycline is rarely used in female patients. [37] Minocycline's vestibular side effects typically resolve after discontinuation of the drug. [38] [39] [40] [41]

Symptoms of an allergic reaction include rash, itching, swelling, severe dizziness, and trouble breathing. [33] Minocycline has also been reported to very rarely cause idiopathic intracranial hypertension (pseudotumor cerebri), [42] a side effect also more common in female patients, potentially leading to permanent vision damage if not recognized early and treated. [43]

Contrary to most other tetracycline antibiotics (doxycycline excluded), minocycline may be used in those with kidney disease, but may aggravate systemic lupus erythematosus. [44] It may also trigger or unmask autoimmune hepatitis. [45]

Minocycline can cause the rare condition of secondary intracranial hypertension, which has initial symptoms of headache, visual disturbances, dizziness, vomiting, and confusion. [46] Brain swelling and rheumatoid arthritis are rare side effects of minocycline in some people. [47]

Minocycline, like most tetracyclines, becomes dangerous past its expiration date. [48] While most prescription drugs lose potency after their expiration dates, tetracyclines are known to become toxic over time. Expired tetracyclines can cause serious damage to the kidney due to the formation of a degradation product, anhydro-4-epitetracycline. [48] Minocycline's absorption is impaired if taken at the same time of day as calcium or iron supplements. Unlike some of the other tetracycline group antibiotics, it can be taken with calcium-rich foods such as milk, although this does reduce the absorption slightly. [49]

Minocycline, like other tetracyclines, is associated with esophageal irritation and ulceration if insufficient fluids are taken with the drug before sleep. [50]

A 2007 study suggested that minocycline harms amyotrophic lateral sclerosis patients. Patients on minocycline declined more rapidly than those on placebo. The mechanism of this side effect is unknown, although a hypothesis is that the drug exacerbated an autoimmune component of the primary disease. The effect does not seem to be dose-dependent because the patients on high doses did not do worse than those on the low doses. [51]

The use of minocycline in acne vulgaris has been associated with skin and gut dysbiosis (see antibiotic misuse). [52]

Interactions

The combination of minocycline with dairy, antacids, calcium and magnesium supplements, iron products, laxatives containing magnesium, or bile acid sequestrants may decrease minocycline's effectiveness by forming chelates. Combining it with isotretinoin, acitretin or other retinoids can increase the risk for intracranial hypertension. Minocycline significantly reduces concentrations of the anti-HIV drug atazanavir in the body. [5] [53]

Pharmacology

Mechanism of action

Pharmacokinetics

Minocycline is quickly and nearly completely absorbed from the upper part of the small intestine. Taking it together with food, including milk, has no relevant influence on resorption. It reaches highest blood plasma concentrations after one to two hours and has a plasma protein binding of 70–75%. The substance penetrates into almost all tissues; very high concentrations are found in the gallbladder and liver. It crosses the blood–brain barrier better than doxycycline and other tetracyclines, reaching therapeutically relevant concentrations in the cerebrospinal fluid and also in inflamed meninges. [5] [54]

Minocycline is inactivated by metabolization in the liver to about 50%. The rest is predominantly excreted into the gut (in part via the gallbladder, in part directly from blood vessels) and eliminated via the feces. About 10–15% are eliminated via the kidneys. The biological half-life is 14–22 (11–26 [4] ) hours in healthy people, up to 30 hours in those with kidney failure, [4] and significantly longer in those with liver disease. [5] [54]

Chemistry

The drug is used in form of minocycline hydrochloride dihydrate, [54] which is sparingly soluble in water and slightly soluble in ethanol. Minocycline reacts acidic in aqueous solution. [5]

History

Minocycline was patented in 1961 and came into commercial use in 1971. [9] A topical foam for treatment of acne was approved in 2019. [3]

Society and culture

Brand names

It is available as a generic medication. [7]

Research

Early research has found a tentative benefit from minocycline in schizophrenia, [56] with several trials underway. [57] A 2014 meta-analysis found minocycline may reduce negative and total symptom scores and was well tolerated. [58]

Research is examining the possible neuroprotective and anti-inflammatory effects of minocycline against the progression of a group of neurodegenerative disorders including multiple sclerosis, rheumatoid arthritis, Huntington's disease, and Parkinson's disease. [59] [60] [61] [62] As mentioned above, minocycline harms ALS patients.[ citation needed ]

Minocycline is also known to indirectly inhibit inducible nitric oxide synthase. [63]

A trial found no difference between minocycline and placebo in people with Alzheimers' disease. [64] Minocycline also has been used as a "last-ditch" treatment for toxoplasmosis in AIDS patients. [65] Minocycline is somewhat neuroprotective in mouse models of Huntington's disease. [66]

A 2007 study reported the impact of the antibiotic minocycline on clinical and magnetic resonance imaging (MRI) outcomes and serum immune molecules in 40 MS patients over 24 months of open-label minocycline treatment. Despite a moderately high pretreatment relapse rate in the patient group prior to treatment (1.3/year pre-enrollment; 1.2/year during a three-month baseline period), no relapses occurred between months 6 and 24 on minocycline. Also, despite significant MRI disease-activity pretreatment (19/40 scans had gadolinium-enhancing activity during a three-month run-in), the only patient with gadolinium-enhancing lesions on MRI at 12 and 24 months was on half-dose minocycline. Levels of interleukin-12 (IL-12), which at high levels might antagonize the proinflammatory IL-12 receptor, were elevated over 18 months of treatment, as were levels of soluble vascular cell adhesion molecule-1 (VCAM-1). The activity of matrix metalloproteinase-9 was decreased by treatment. Clinical and MRI outcomes in this study were supported by systemic immunological changes and call for further investigation of minocycline in MS. [67] [68] [69]

Minocycline has been studied for treatment-resistant depression. According to a systematic review based on four clinical trials, "There is no significant difference with minocycline compared to placebo for depression not responding to first-line antidepressant therapy." [70]

In ongoing research and trial, minocycline demonstrated efficacy and seems a promising neuroprotective agent in acute stroke patients, especially in AIS subgroup. Further RCTs are needed to evaluate the efficacy and safety of minocycline among ICH patients. [71]

Several preclinical studies (in vitro cell cultures and animal models) suggest that minocycline may have otoprotective benefits. Animal models indicate it could potentially reduce noise-induced and blast-induced hearing loss, possibly by protecting hair cells and mitigating inflammation. [72] [73] In vitro and animal studies also show minocycline may help decrease ototoxicity from certain drugs like gentamicin, [74] neomycin, [75] and cisplatin. [76] [77]

Some early studies suggest that minocycline may be beneficial as an add-on treatment for moderate-to-severe obsessive-compulsive disorder (OCD) when used with an SSRI. [78] [79]

Data from cellular and animal models

Related Research Articles

<span class="mw-page-title-main">Acne</span> Skin condition characterized by pimples

Acne, also known as acne vulgaris, is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and possible scarring. It primarily affects skin with a relatively high number of oil glands, including the face, upper part of the chest, and back. The resulting appearance can lead to lack of confidence, anxiety, reduced self-esteem, and, in extreme cases, depression or thoughts of suicide.

<span class="mw-page-title-main">Isotretinoin</span> Medication primarily used to treat severe acne

Isotretinoin, also known as 13-cis-retinoic acid and sold under the brand name Accutane among others, is a medication primarily used to treat severe acne. It is also used to prevent certain skin cancers, and in the treatment of other cancers. It is used to treat harlequin-type ichthyosis, a usually lethal skin disease, and lamellar ichthyosis. It is a retinoid, meaning it is related to vitamin A, and is found in small quantities naturally in the body. Its isomer, tretinoin, is also an acne drug.

<span class="mw-page-title-main">Broad-spectrum antibiotic</span> Treatment for a wide range of bacteria

A broad-spectrum antibiotic is an antibiotic that acts on the two major bacterial groups, Gram-positive and Gram-negative, or any antibiotic that acts against a wide range of disease-causing bacteria. These medications are used when a bacterial infection is suspected but the group of bacteria is unknown or when infection with multiple groups of bacteria is suspected. This is in contrast to a narrow-spectrum antibiotic, which is effective against only a specific group of bacteria. Although powerful, broad-spectrum antibiotics pose specific risks, particularly the disruption of native, normal bacteria and the development of antimicrobial resistance. An example of a commonly used broad-spectrum antibiotic is ampicillin.

<span class="mw-page-title-main">Hidradenitis suppurativa</span> Human disease

Hidradenitis suppurativa (HS), sometimes known as acne inversa or Verneuil's disease, is a long-term dermatological condition characterized by the occurrence of inflamed and swollen lumps. These are typically painful and break open, releasing fluid or pus. The areas most commonly affected are the underarms, under the breasts, perineum, buttocks, and the groin. Scar tissue remains after healing. HS may significantly limit many everyday activities, for instance, walking, hugging, moving, and sitting down. Sitting disability may occur in patients with lesions in sacral, gluteal, perineal, femoral, groin or genital regions; and prolonged periods of sitting down can also worsen the condition of the skin of these patients.

<i>Cutibacterium acnes</i> Species of bacterium

Cutibacterium acnes is the relatively slow-growing, typically aerotolerant anaerobic, gram-positive bacterium (rod) linked to the skin condition of acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. Its genome has been sequenced and a study has shown several genes can generate enzymes for degrading skin and proteins that may be immunogenic.

<span class="mw-page-title-main">Tretinoin</span> Medication

Tretinoin, also known as all-trans retinoic acid (ATRA), is a medication used for the treatment of acne and acute promyelocytic leukemia. For acne, it is applied to the skin as a cream, gel or ointment. For leukemia, it is taken by mouth for up to three months. Topical tretinoin is also the most extensively investigated retinoid therapy for photoaging.

<span class="mw-page-title-main">Dapsone</span> Antibiotic medication

Dapsone, also known as 4,4'-sulfonyldianiline (SDA) or diaminodiphenyl sulfone (DDS), is an antibiotic commonly used in combination with rifampicin and clofazimine for the treatment of leprosy. It is a second-line medication for the treatment and prevention of pneumocystis pneumonia and for the prevention of toxoplasmosis in those who have poor immune function. Additionally, it has been used for acne, dermatitis herpetiformis, and various other skin conditions. Dapsone is available both topically and by mouth.

<span class="mw-page-title-main">Doxycycline</span> Tetracycline-class antibiotic

Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. It is used to treat bacterial pneumonia, acne, chlamydia infections, Lyme disease, cholera, typhus, and syphilis. It is also used to prevent malaria. Doxycycline may be taken by mouth or by injection into a vein.

<span class="mw-page-title-main">Rosacea</span> Skin condition resulting in redness, pimples and swelling, usually on the face

Rosacea is a long-term skin condition that typically affects the face. It results in redness, pimples, swelling, and small and superficial dilated blood vessels. Often, the nose, cheeks, forehead, and chin are most involved. A red, enlarged nose may occur in severe disease, a condition known as rhinophyma.

<span class="mw-page-title-main">Pemphigus</span> Blistering autoimmune diseases

Pemphigus is a rare group of blistering autoimmune diseases that affect the skin and mucous membranes. The name is derived from the Greek root pemphix, meaning "blister".

<span class="mw-page-title-main">Demeclocycline</span> Chemical compound

Demeclocycline is a tetracycline antibiotic which was derived from a mutant strain of Streptomyces aureofaciens.

<span class="mw-page-title-main">Tigecycline</span> Chemical compound

Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline class drug that is administered intravenously. It was developed in response to the growing rate of antibiotic resistant bacteria such as Staphylococcus aureus, Acinetobacter baumannii, and E. coli. As a tetracycline derivative antibiotic, its structural modifications has expanded its therapeutic activity to include Gram-positive and Gram-negative organisms, including those of multi-drug resistance.

<span class="mw-page-title-main">Tetracycline antibiotics</span> Type of broad-spectrum antibiotic

Tetracyclines are a group of broad-spectrum antibiotic compounds that have a common basic structure and are either isolated directly from several species of Streptomyces bacteria or produced semi-synthetically from those isolated compounds. Tetracycline molecules comprise a linear fused tetracyclic nucleus to which a variety of functional groups are attached. Tetracyclines are named after their four ("tetra-") hydrocarbon rings ("-cycl-") derivation ("-ine"). They are defined as a subclass of polyketides, having an octahydrotetracene-2-carboxamide skeleton and are known as derivatives of polycyclic naphthacene carboxamide. While all tetracyclines have a common structure, they differ from each other by the presence of chloro, methyl, and hydroxyl groups. These modifications do not change their broad antibacterial activity, but do affect pharmacological properties such as half-life and binding to proteins in serum.

<span class="mw-page-title-main">Pemphigoid</span> Autoimmune blistering diseases

Pemphigoid is a group of rare autoimmune blistering diseases of the skin and mucous membranes. As its name indicates, pemphigoid is similar in general appearance to pemphigus, however unlike pemphigus, pemphigoid does not feature acantholysis, a loss of connections between skin cells.

<span class="mw-page-title-main">Nadifloxacin</span> Chemical compound

Nadifloxacin is a topical fluoroquinolone antibiotic for the treatment of acne vulgaris. It is also used to treat bacterial skin infections.

<span class="mw-page-title-main">Pimple</span> Type of comedo

A pimple or zit is a kind of comedo that results from excess sebum and dead skin cells getting trapped in the pores of the skin. In its aggravated state, it may evolve into a pustule or papule. Pimples can be treated by acne medications, antibiotics, and anti-inflammatories prescribed by a physician, or various over the counter remedies purchased at a pharmacy.

Infantile acne is a form of acne that begins in very young children. Typical symptoms include inflammatory and noninflammatory lesions, papules and pustules most commonly present on the face. No cause of infantile acne has been established but it may be caused by increased sebaceous gland secretions due to elevated androgens, genetics and the fetal adrenal gland causing increased sebum production. Infantile acne can resolve by itself by age 1 or 2. However, treatment options include topical benzyl peroxide, topical retinoids and topical antibiotics in most cases.

Childhood granulomatous periorificial dermatitis (CGPD), is a rare benign granulomatous skin disease of unknown cause. The disorder was first described in 1970 by Gianotti in a case series of five children. CGPD is more common in boys than girls.

<span class="mw-page-title-main">Antimicrobial spectrum</span> Method of assessing antibiotics

The antimicrobial spectrum of an antibiotic means the range of microorganisms it can kill or inhibit. Antibiotics can be divided into broad-spectrum antibiotics, extended-spectrum antibiotics and narrow-spectrum antibiotics based on their spectrum of activity. Detailedly, broad-spectrum antibiotics can kill or inhibit a wide range of microorganisms; extended-spectrum antibiotic can kill or inhibit Gram positive bacteria and some Gram negative bacteria; narrow-spectrum antibiotic can only kill or inhibit limited species of bacteria.

<span class="mw-page-title-main">Ototoxic medication</span>

Ototoxicity is defined as the toxic effect on the functioning of the inner ear, which may lead to temporary or permanent hearing loss (cochleotoxic) and balancing problems (vestibulotoxic). Drugs or pharmaceutical agents inducing ototoxicity are regarded as ototoxic medications.

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