Oteseconazole

Last updated

Oteseconazole
Oteseconazole.svg
Clinical data
Trade names Vivjoa
Other namesVT-1161
License data
Routes of
administration 		By mouth
Drug class Antifungal
ATC code
Legal status
Legal status
Identifiers
  • (2R)-2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-yl]propan-2-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.277.989 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H16F7N5O2
Molar mass 527.403 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1C2=CN=C(C=C2)C([C@](CN3C=NN=N3)(C4=C(C=C(C=C4)F)F)O)(F)F)OCC(F)(F)F
  • InChI=1S/C23H16F7N5O2/c24-16-4-7-18(19(25)9-16)21(36,11-35-13-32-33-34-35)23(29,30)20-8-3-15(10-31-20)14-1-5-17(6-2-14)37-12-22(26,27)28/h1-10,13,36H,11-12H2/t21-/m0/s1
  • Key:IDUYJRXRDSPPRC-NRFANRHFSA-N

Oteseconazole, a novel orally bioavailable and selective inhibitor of fungal cytochrome P450 enzyme 51 (CYP51), has shown promising efficacy in the treatment of recurrent vulvovaginal candidiasis (RVVC) in patients. [2] [3]

Contents

Marketed under the brand name Vivjoa, this medication was developed by Mycovia Pharmaceuticals and received approval for medicinal use from United States Food and Drug Administration (US FDA) in April 2022. [1] [4] [5]

Society and culture

Names

Oteseconazole is the international nonproprietary name (INN). [6]

Mechanism of action

Oteseconazole targets cytochrome P450 enzymes 51 (CYP51), which a play crucial role in maintaining the integrity and growth of fungal cell membranes. Through inhibition of these enzymes, oteseconazole prevents the synthesis of ergosterol, a key component of fungal cell membranes development. This disruption in ergosterol production leads to fungal membranes permeability, ultimately causing cell death. [2] [3] [7]

Oteseconazole exhibits selective inhibition of fungal CYP51 and has shown remarkable potency against Candida species during invitro pharmacological studies. [8] This targeted action of oteseconazole makes it a highly effective choice for treating RVVC. [2] [9] Additionally, oteseconazole was found to possess superior activity against certain fungi, such as Candida glabrata compared to commonly used antifungals. [10]

Adverse effect and interaction

Oteseconazole has exhibited an outstanding tolerability profile and a low occurrence of adverse effects in clinical trials. In a phase 3 study, the incidence of treatment-emergent adverse events (TEAEs) was comparable between the oteseconazole and fluconazole/placebo groups, with the majority of TEAEs being of mild or moderate severity. [9] No serious adverse events related to the drug, as well as no adverse effects on liver function or QT intervals, were reported. [9] However, it is important to acknowledge that, like any medication, there is a potential risk of adverse effects. Therefore, it is crucial to consult with a healthcare provider prior to initiating oteseconazole or any other medication.

There is currently limited information available on oteseconazole interactions with other medications. The prescribing information for oteseconazole indicates that it is a moderate inhibitor of the CYP3A4 enzyme, suggesting that it may potentially increase the exposure of co-administered medications that are primarily metabolized by CYP3A4. [3] Therefore, patients who are taking medications metabolized by CYP3A4 should be closely monitored for any signs of toxicity or adverse effects when using oteseconazole. [3] It is crucial to have a discussion with a healthcare provider about the use of any medications or supplements to ensure safe and effective usage.

Related Research Articles

<span class="mw-page-title-main">Candidiasis</span> Fungal infection due to any type of Candida

Candidiasis is a fungal infection due to any species of the genus Candida. When it affects the mouth, in some countries it is commonly called thrush. Signs and symptoms include white patches on the tongue or other areas of the mouth and throat. Other symptoms may include soreness and problems swallowing. When it affects the vagina, it may be referred to as a yeast infection or thrush. Signs and symptoms include genital itching, burning, and sometimes a white "cottage cheese-like" discharge from the vagina. Yeast infections of the penis are less common and typically present with an itchy rash. Very rarely, yeast infections may become invasive, spreading to other parts of the body. This may result in fevers, among other symptoms.

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

Clarithromycin, sold under the brand name Biaxin among others, is an antibiotic used to treat various bacterial infections. This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease, among others. Clarithromycin can be taken by mouth as a tablet or liquid or can be infused intravenously.>

<span class="mw-page-title-main">Antifungal</span> Pharmaceutical fungicide or fungistatic used to treat and prevent mycosis

An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC). The evolution of antifungal resistance is a growing threat to health globally.

<span class="mw-page-title-main">Itraconazole</span> Medication used to treat fungal infections

Itraconazole, sometimes abbreviated ITZ, is an antifungal medication used to treat a number of fungal infections. This includes aspergillosis, blastomycosis, coccidioidomycosis, histoplasmosis, and paracoccidioidomycosis. It may be given by mouth or intravenously.

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

Nystatin, sold under the brand name Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be used to prevent candidiasis in those who are at high risk. Nystatin may be used by mouth, in the vagina, or applied to the skin.

<span class="mw-page-title-main">Amphotericin B</span> Antifungal and antiparasitaric chemical compound

Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include mucormycosis, aspergillosis, blastomycosis, candidiasis, coccidioidomycosis, and cryptococcosis. For certain infections it is given with flucytosine. It is typically given intravenously.

<span class="mw-page-title-main">Ketoconazole</span> Antifungal chemical compound

Ketoconazole, sold under the brand name Nizoral among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.

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

Fluconazole is an antifungal medication used for a number of fungal infections. This includes candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and tinea versicolor. It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts. It is given either by mouth or by injection into a vein.

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

Miconazole, sold under the brand name Monistat among others, is an antifungal medication used to treat ring worm, pityriasis versicolor, and yeast infections of the skin or vagina. It is used for ring worm of the body, groin, and feet. It is applied to the skin or vagina as a cream or ointment.

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

Terbinafine, sold under the brand name Lamisil among others, is an antifungal medication used to treat pityriasis versicolor, fungal nail infections, and ringworm including jock itch and athlete's foot. It is either taken by mouth or applied to the skin as a cream or ointment. The cream and ointment are not effective for nail infections.

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

Terconazole is an antifungal drug used to treat vaginal yeast infection. It comes as a lotion or a suppository and disrupts the biosynthesis of fats in a yeast cell. It has a relatively broad spectrum compared to azole compounds but not triazole compounds. Testing shows that it is a suitable compound for prophylaxis for those that suffer from chronic vulvovaginal candidiasis.

<span class="mw-page-title-main">Posaconazole</span> Pharmaceutical drug

Posaconazole, sold under the brand name Noxafil among others, is a triazole antifungal medication.

<span class="mw-page-title-main">Echinocandin</span> Group of chemical compounds

Echinocandins are a class of antifungal drugs that inhibit the synthesis of β-glucan in the fungal cell wall via noncompetitive inhibition of the enzyme 1,3-β glucan synthase. The class has been termed the "penicillin of antifungals," along with the related papulacandins, as their mechanism of action resembles that of penicillin in bacteria. β-glucans are carbohydrate polymers that are cross-linked with other fungal cell wall components, the fungal equivalent to bacterial peptidoglycan. Caspofungin, micafungin, and anidulafungin are semisynthetic echinocandin derivatives with limited clinical use due to their solubility, antifungal spectrum, and pharmacokinetic properties.

<span class="mw-page-title-main">Sterol 14-demethylase</span> Class of enzymes

In enzymology, a sterol 14-demethylase (EC 1.14.13.70) is an enzyme of the cytochrome P450 (CYP) superfamily. It is any member of the CYP51 family. It catalyzes a chemical reaction such as:

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

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock itch. It can be taken by mouth or applied as a cream to the skin or in the vagina.

<span class="mw-page-title-main">Vaginal yeast infection</span> Medical condition

Vaginal yeast infection, also known as candidal vulvovaginitis and vaginal thrush, is excessive growth of yeast in the vagina that results in irritation. The most common symptom is vaginal itching, which may be severe. Other symptoms include burning with urination, a thick, white vaginal discharge that typically does not smell bad, pain during sex, and redness around the vagina. Symptoms often worsen just before a woman's period.

<i>Candida tropicalis</i> Species of fungus

Candida tropicalis is a species of yeast in the genus Candida. It is a common pathogen in neutropenic hosts, in whom it may spread through the bloodstream to peripheral organs. For invasive disease, treatments include amphotericin B, echinocandins, or extended-spectrum triazole antifungals.

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

Ibrexafungerp, sold under the brand name Brexafemme, is an antifungal medication used to treat vulvovaginal candidiasis (VVC). It is taken orally. It is also currently undergoing clinical trials for other indications via an intravenous (IV) formulation. An estimated 75% of women will have at least one episode of VVC and 40 to 45% will have two or more episodes in their lifetime.

Topical antifungaldrugs are used to treat fungal infections on the skin, scalp, nails, vagina or inside the mouth. These medications come as creams, gels, lotions, ointments, powders, shampoos, tinctures and sprays. Most antifungal drugs induce fungal cell death by destroying the cell wall of the fungus. These drugs inhibit the production of ergosterol, which is a fundamental component of the fungal cell membrane and wall.

<span class="mw-page-title-main">TOL-463</span> Combination drug

TOL-463 is an anti-infective medication which is under development for the treatment of bacterial vaginosis (BV) and vulvovaginal candidiasis (VVC). It is a boric acid-based vaginal anti-infective enhanced with ethylenediaminetetraacetic acid (EDTA) which was designed to have improved activity against vaginal bacterial and fungal biofilms while sparing protective lactobacilli. EDTA enhances the antimicrobial activity of boric acid and improves its efficacy against relevant biofilms. In a small phase 2 randomized controlled trial, TOL-463 as an insert or gel achieved clinical cure rates of 50–59% against BV and 81–92% against VVC in women who had one or both conditions. It was effective and safe in the study, though it was without indication of superiority over other antifungal medications for VVC. The cure rates against BV with TOL-463 were said to be comparable to those with recently approved antibiotic treatments like single-dose oral secnidazole (58%) and single-dose metronidazole vaginal gel (41%). As of May 2019, TOL-463 is in phase 2 clinical trials for the treatment of BV and VVC. It was originated by Toltec Pharmaceuticals and is under development by Toltec Pharmaceuticals and the National Institute of Allergy and Infectious Diseases.

References

  1. 1 2 "Vivjoa- oteseconazole capsule". DailyMed. U.S. National Library of Medicine. 12 July 2022. Retrieved 21 January 2023.
  2. 1 2 3 Sobel JD, Nyirjesy P (December 2021). "Oteseconazole: an advance in treatment of recurrent vulvovaginal candidiasis". Future Microbiology. 16 (18): 1453–1461. doi: 10.2217/fmb-2021-0173 . PMID   34783586. S2CID   244131114.
  3. 1 2 3 4 De SK (2023). "Oteseconazole: First Approved Orally Bioavailable and Selective CYP51 Inhibitor for the Treatment of Patients with Recurrent Vulvovaginal Candidiasis". Current Medicinal Chemistry. 30 (37): 4170–4175. doi:10.2174/0929867330666230220130024. PMID   36803759. S2CID   257066627.
  4. ↑ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 26 June 2023.
  5. ↑ "FDA Approves Mycovia Pharmaceuticals' VIVJOA™ (oteseconazole), the First and Only FDA-Approved Medication for Recurrent Vulvovaginal Candidiasis (Chronic Yeast Infection)". www.businesswire.com. 28 April 2022. Retrieved 26 June 2023.
  6. ↑ World Health Organization (2016). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 76". WHO Drug Information. 30 (3). hdl: 10665/331020 .
  7. ↑ Butler SK, Ayinon C (November 2022). "Treating recurrent vulvovaginal candidiasis". OBG Manag. 34 (11): 22–24, 28–30, 32. doi: 10.12788/obgm.0238 . S2CID   257013981 . Retrieved 26 June 2023– via www.mdedge.com.
  8. ↑ Neha, Kumar S, Madaan V, Sharma DV, Sharma DM, Soni SL, Sharma AK (15 September 2022). "Oteseconazole: A Review". Journal of Biomedical and Pharmaceutical Research. 11 (5). doi: 10.32553/jbpr.v11i5.918 . ISSN   2279-0594. S2CID   252343000.
  9. 1 2 3 Martens MG, Maximos B, Degenhardt T, Person K, Curelop S, Ghannoum M, Brand S (November 2021). "107. A phase 3, randomized, double-blind study to evaluate the efficacy and safety of oteseconazole (VT-1161) oral capsules versus fluconazole and placebo in the treatment of acute vulvovaginal candidiasis episodes in subjects with recurrent vulvovaginal candidiasis (ultraViolet)". Open Forum Infectious Diseases. 8 (Supplement_1). US: Oxford University Press: S66–S67. doi:10.1093/ofid/ofab466.107. PMC   8644338 .
  10. ↑ Gupta AK, Talukder M, Venkataraman M (December 2022). "Review of the alternative therapies for onychomycosis and superficial fungal infections: posaconazole, fosravuconazole, voriconazole, oteseconazole". International Journal of Dermatology. 61 (12): 1431–1441. doi:10.1111/ijd.15999. PMID   34882787. S2CID   245013623.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.