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 is used in the treatment of tuberculosis.^[1]^[2]^[3] It is the mesylate (methanesulfonate) ester of 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 ester at the same position as that of the acetyl ester 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]

Neothetazone is an antibiotic combination of methaniazide (neotizide) and thioacetazone which is or was previously used in the treatment of tuberculosis.^[5] It has been associated with a case report of gigantomastia.^[5]^[6]^[7] Similarly, there have been a variety of case reports in the literature of gynecomastia associated with isoniazid treatment.^[8]

References

^ ^a ^b ^c J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 709–. ISBN 978-1-4757-2085-3.
^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.
^ https://www.drugs.com/international/methaniazide.html
^ Bernard Testa; Joachim M. Mayer (August 2003). Hydrolysis in Drug and Prodrug Metabolism. John Wiley & Sons. pp. 149–. ISBN 978-3-906390-25-3.
^ ^a ^b 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.
^ Sakai Y, Wakamatsu S, Ono K, Kumagai N (2002). "Gigantomastia induced by bucillamine". Annals of Plastic Surgery. 49 (2): 193–5. 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.
^ 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.
^ Khan A, Agarwal R (2012). "Isoniazid related gynecomastia: Description of a case and systematic review of literature". Lung India. 29 (2): 189–91. doi:10.4103/0970-2113.95343. PMC 3354502. PMID 22628943.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 709–. ISBN 978-1-4757-2085-3.

[MortonHall2012-2] I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.

[Drugs.com-3] ttps://www.drugs.com/international/methaniazide.html

[TestaMayer2003-4] Bernard Testa; Joachim M. Mayer (August 2003). Hydrolysis in Drug and Prodrug Metabolism. John Wiley & Sons. pp. 149–. ISBN 978-3-906390-25-3.

[SAMJ1970-5] 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.

[pmid12187348-6] Sakai Y, Wakamatsu S, Ono K, Kumagai N (2002). "Gigantomastia induced by bucillamine". Annals of Plastic Surgery. 49 (2): 193–5. 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.

[pmid18054304-7] 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.

[pmid22628943-8] Khan A, Agarwal R (2012). "Isoniazid related gynecomastia: Description of a case and systematic review of literature". Lung India. 29 (2): 189–91. doi:10.4103/0970-2113.95343. PMC 3354502. PMID 22628943.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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