Methaniazide

Last updated
Methaniazide
Methaniazide.svg
Clinical data
Trade names Erbazid, Neoiscotin, Neo-Iscotin, Nesticide, Neotizide, Neo-Tizide
Other namesMetaniazide; Neotizide; Isoniazid methanesulfonate; Isoniazid methanosulfonate; Isoniazid mesylate; Isonicotinic acid hydrazide methanesulfonate
Identifiers
  • [2-(Pyridine-4-carbonyl)hydrazinyl]methanesulfonic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.033.264 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C7H9N3O4S
Molar mass 231.23 g·mol−1
3D model (JSmol)
  • C1=CN=CC=C1C(=O)NNCS(=O)(=O)O
  • InChI=1S/C7H9N3O4S/c11-7(6-1-3-8-4-2-6)10-9-5-15(12,13)14/h1-4,9H,5H2,(H,10,11)(H,12,13,14)
  • Key:GQZQCROBCYNTMU-UHFFFAOYSA-N

Methaniazide, brand name Neotizide among others, is an antibiotic which was used in the treatment of tuberculosis. [1] [2] [3] It is a derivative of methanesulfonic acid and isoniazid, which is also an antituberculosis drug but has comparatively been far more widely known and used. [1] Isoniazid is a prodrug of isonicotinic acid, and acetylisoniazid, a metabolite of isoniazid, is a metabolic intermediate through which most of the isonicotinic acid is formed. [4] Methaniazide features its mesylate group at the same position as that of the acetyl group in acetylisoniazid, and so methaniazide probably acts as a prodrug of isonicotinic acid similarly to isoniazid and acetylisoniazid. Methaniazide is used as the sodium salt. [1] It was never approved for use or sale in the United States. [5]

Neothetazone is an antibiotic combination of methaniazide (neotizide) and thioacetazone which was previously used in the treatment of tuberculosis. [6] It has been associated with a case report of gigantomastia. [6] [7] [8] Similarly, there have been a variety of case reports in the literature of gynecomastia associated with isoniazid treatment. [9]

Related Research Articles

<span class="mw-page-title-main">Isoniazid</span> Antibiotic for treatment of tuberculosis

Isoniazid, also known as isonicotinic acid hydrazide (INH), is an antibiotic used for the treatment of tuberculosis. For active tuberculosis, it is often used together with rifampicin, pyrazinamide, and either streptomycin or ethambutol. For latent tuberculosis, it is often used alone. It may also be used for atypical types of mycobacteria, such as M. avium, M. kansasii, and M. xenopi. It is usually taken by mouth, but may be used by injection into muscle.

<span class="mw-page-title-main">Rifamycin</span> Group of antibiotics

The rifamycins are a group of antibiotics that are synthesized either naturally by the bacterium Amycolatopsis rifamycinica or artificially. They are a subclass of the larger family of ansamycins. Rifamycins are particularly effective against mycobacteria, and are therefore used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections.

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

Rifampicin, also known as rifampin, is an ansamycin antibiotic used to treat several types of bacterial infections, including tuberculosis (TB), Mycobacterium avium complex, leprosy, and Legionnaires' disease. It is almost always used together with other antibiotics with two notable exceptions: when given as a "preferred treatment that is strongly recommended" for latent TB infection; and when used as post-exposure prophylaxis to prevent Haemophilus influenzae type b and meningococcal disease in people who have been exposed to those bacteria. Before treating a person for a long period of time, measurements of liver enzymes and blood counts are recommended. Rifampicin may be given either by mouth or intravenously.

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

Cimetidine, sold under the brand name Tagamet among others, is a histamine H2 receptor antagonist that inhibits stomach acid production. It is mainly used in the treatment of heartburn and peptic ulcers.

<span class="mw-page-title-main">Candesartan</span> Angiotensin II receptor antagonist

Candesartan is an angiotensin receptor blocker used mainly for the treatment of high blood pressure and congestive heart failure. Candesartan has a very low maintenance dose. Like Olmesartan, the metabolism of the drug is unusual as it is a cascading prodrug. Candesartan has good bioavailibility and is the most potent by weight of the AT-1 receptor antagonists.

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

Penicillamine, sold under the brand name of Cuprimine among others, is a medication primarily used for the treatment of Wilson's disease. It is also used for people with kidney stones who have high urine cystine levels, rheumatoid arthritis, and various heavy metal poisonings. It is taken by mouth.

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

Pyrazinamide is a medication used to treat tuberculosis. For active tuberculosis, it is often used with rifampicin, isoniazid, and either streptomycin or ethambutol. It is not generally recommended for the treatment of latent tuberculosis. It is taken by mouth.

<span class="mw-page-title-main">4-Aminosalicylic acid</span> Anti-tuberculosis and anti-inflammatory drug

4-Aminosalicylic acid, also known as para-aminosalicylic acid (PAS) and sold under the brand name Paser among others, is an antibiotic primarily used to treat tuberculosis. Specifically it is used to treat active drug resistant tuberculosis together with other antituberculosis medications. It has also been used as a second line agent to sulfasalazine in people with inflammatory bowel disease such as ulcerative colitis and Crohn's disease. It is typically taken by mouth.

<span class="mw-page-title-main">Iproniazid</span> Antidepressant

Iproniazid is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France until its discontinuation in 2015.

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

Rifapentine, sold under the brand name Priftin, is an antibiotic used in the treatment of tuberculosis. In active tuberculosis it is used together with other antituberculosis medications. In latent tuberculosis it is typically used with isoniazid. It is taken by mouth.

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

Estramustine phosphate (EMP), also known as estradiol normustine phosphate and sold under the brand names Emcyt and Estracyt, is a dual estrogen and chemotherapy medication which is used in the treatment of prostate cancer in men. It is taken multiple times a day by mouth or by injection into a vein.

<span class="mw-page-title-main">Breast hypertrophy</span> Human disease

Breast hypertrophy is a rare medical condition of the breast connective tissues in which the breasts become excessively large. The condition is often divided based on the severity into two types, macromastia and gigantomastia. Hypertrophy of the breast tissues may be caused by increased histologic sensitivity to certain hormones such as female sex hormones, prolactin, and growth factors. Breast hypertrophy is a benign progressive enlargement, which can occur in both breasts (bilateral) or only in one breast (unilateral). It was first scientifically described in 1648.

<span class="mw-page-title-main">Breast implant</span> Prosthesis used to change the size, shape, and contour of a persons breast

A breast implant is a prosthesis used to change the size, shape, and contour of a person's breast. In reconstructive plastic surgery, breast implants can be placed to restore a natural looking breast following a mastectomy, to correct congenital defects and deformities of the chest wall or, cosmetically, to enlarge the appearance of the breast through breast augmentation surgery.

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

Ethionamide is an antibiotic used to treat tuberculosis. Specifically it is used, along with other antituberculosis medications, to treat active multidrug-resistant tuberculosis. It is no longer recommended for leprosy. It is taken by mouth.

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

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth.

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

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

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

Epitiostanol, sold under the brand name Thiodrol, is an injected antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was described in the literature in 1965 and has been marketed in Japan as an antineoplastic agent for the treatment of breast cancer since 1977.

SQ109 is a drug undergoing development for treatment of tuberculosis.

<span class="mw-page-title-main">Gynecomastia</span> Endocrine system disorder of human male breast

Gynecomastia is the abnormal non-cancerous enlargement of one or both breasts in males due to the growth of breast tissue as a result of a hormone imbalance between estrogens and androgens. Gynecomastia can cause significant psychological distress or unease.

Methaniazide/thioacetazone, sold under the brand name Neothetazone, is an antibiotic combination of methaniazide (neotizide) and thioacetazone that is or was very commonly used in the treatment of tuberculosis. It has been implicated as a cause of gigantomastia in a single 1970 case report, and, along with D-penicilliamine, bucillamine, ciclosporin, and indinavir, is one of the only drugs to have been associated with gigantomastia.

References

  1. 1 2 3 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 709–. ISBN   978-1-4757-2085-3.
  2. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN   978-94-011-4439-1.
  3. "Methaniazide". Drugs.com. Archived from the original on 2019-08-08. Retrieved 2017-06-24.
  4. Testa B, Mayer JM (August 2003). "The Hydrolysis of Amides". Hydrolysis in Drug and Prodrug Metabolism. John Wiley & Sons. pp. 149–. doi:10.1002/9783906390444.ch4. ISBN   978-3-906390-25-3.
  5. "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 2022-08-11.
  6. 1 2 SAMJ. Medical Association of South Africa. 1970. pp. 449–450. Diffuse hypertrophy of the breasts seems to have been associated in this patient with treatment with Neothetazone, which consists of neotizide and thiacetazone, and which is very commonly used in the treatment of tuberculosis.
  7. Sakai Y, Wakamatsu S, Ono K, Kumagai N (August 2002). "Gigantomastia induced by bucillamine". Annals of Plastic Surgery. 49 (2): 193–195. doi:10.1097/00000637-200208000-00013. PMID   12187348. Drug-induced mammary hyperplasias have been reported as rare complications of D-penicillamine and Neothetazone. [...] It is rare for breast hypertrophy to be induced by drugs. In particular, gigantomastia has been reported to be induced by only two drugs: D-penicillamine and the antibiotic neothetazone. [...] In 1970, drug-induced gigantomastia was reported for the first time by Scott.4 It was induced by the antibiotic Neothetazone.
  8. Dancey A, Khan M, Dawson J, Peart F (2008). "Gigantomastia--a classification and review of the literature". Journal of Plastic, Reconstructive & Aesthetic Surgery. 61 (5): 493–502. doi:10.1016/j.bjps.2007.10.041. PMID   18054304.
  9. Khan A, Agarwal R (April 2012). "Isoniazid related gynecomastia: Description of a case and systematic review of literature". Lung India. 29 (2): 189–191. doi: 10.4103/0970-2113.95343 . PMC   3354502 . PMID   22628943.