Fungichromin

Title: Fungichromin
CAS Registry Number: 6834-98-6
Additional Names: Antibiotic A 246; cogomycin; lagosin; pentamycin
Trademarks: Cantricin (Corvi)
Molecular Formula: C35H58O12
Molecular Weight: 670.83
Percent Composition: C 62.66%, H 8.71%, O 28.62%
Literature References: Antifungal polyene macrolide antibiotic, related structurally to filipin, q.v. Isoln from Streptomyces cellulosae: A. A. Tytell et al., Antibiot. Annu. 1954-1955, 716. Isoln (as pentamycin) from S. penticus: S. Umezawa, Y. Tanaka, J. Antibiot. 11A, 26 (1958). Isoln (as lagosin) from S. roseoluteus: C. J. Bessel et al., US 3013947 (1961 to Glaxo). Isoln from S. griseus (FCRC-21): R. C. Pandey et al., Biomed. Mass Spectrom. 7, 93 (1980). Structures: A. C. Cope, H. E. Johnson, J. Am. Chem. Soc. 80, 1504 (1958); A. C. Cope et al., ibid. 84, 2170 (1962); M. L. Dhar et al., J. Chem. Soc. 1964, 842; M. P. Berry, M. C. Whiting, ibid. 862; V. Pozgay et al., J. Antibiot. 29, 472 (1976). Identity of fungichromin with lagosin and cogomycin and comparison of reported physico-chemical constants: R. C. Pandey et al., J. Antibiot. 35, 988 (1982). Biosynthesis and NMR assignment: H. Noguchi et al., J. Am. Chem. Soc. 110, 2938 (1988).
Properties: Light yellow cryst. mp 157-162° (dec). [a]D20 -227.7° (c = 0.53 in DMF). uv max (methanol): 357, 338, 322 nm (E1%1cm 1231, 1250, 786). LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka).
Melting point: mp 157-162° (dec)
Optical Rotation: [a]D20 -227.7° (c = 0.53 in DMF)
Absorption maximum: uv max (methanol): 357, 338, 322 nm (E1%1cm 1231, 1250, 786)
Toxicity data: LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka)
Therap-Cat: Antifungal (topical).
Keywords: Antifungal (Antibiotics); Polyenes.
Fungisterol Funtumine Fura-2 Furaltadone Furametpyr

Pentamycin
Pentamycin.png
Systematic (IUPAC) name
(3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Clinical data
Legal status  ?
Routes Vaginal pessary
Identifiers
ATC code G01AA11
PubChem CID 5358751
ChemSpider 4445390 YesY
Chemical data
Formula C35H58O12 
Mol. mass 670.82782 g/mol
 YesY (what is this?)  (verify)

Pentamycin, also called fungichromin, is a macrolide antibiotic. Pentamycin is a polyene antifungal antibiotic obtained from Streptomyces pentaticus. It is used in the treatment of vaginal candidiasis and for the protozoal infection trichomoniasis. A 3 mg vaginal pessary is inserted once or twice daily for 5-10 days.