Methaniazide

Methaniazide

Clinical data
Trade names	Erbazid, Neoiscotin, Neo-Iscotin, Nesticide, Neotizide, Neo-Tizide
Other names	Metaniazide; Neotizide; Isoniazid methanesulfonate; Isoniazid methanosulfonate; Isoniazid mesylate; Isonicotinic acid hydrazide methanesulfonate
Identifiers
IUPAC name [2-(Pyridine-4-carbonyl)hydrazinyl]methanesulfonic acid
CAS Number	13447-95-5 3804-89-5 (sodium)
PubChem CID	3769
ChemSpider	3637
UNII	GN8S7ZES0F
KEGG	D08198
ChEBI	CHEBI:134943
ChEMBL	ChEMBL2105190
CompTox Dashboard (EPA)	DTXSID2048248
ECHA InfoCard	100.033.264
Chemical and physical data
Formula	C7H9N3O4S
Molar mass	231.23 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C1=CN=CC=C1C(=O)NNCS(=O)(=O)O
InChI 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]

References

1. 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. 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.