MedKoo Cat#: 461627 | Name: Fungichromin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fungichromin, also known as pentamycin, is a polyene macrolide antibiotic produced by Streptomyces species, characterized by a large macrocyclic lactone ring with conjugated double bonds and multiple hydroxyl groups. It exerts antifungal activity by binding to ergosterol in fungal cell membranes, disrupting membrane integrity and causing ion leakage and cell death. Fungichromin shows selective toxicity toward fungal cells and is used in both agricultural and medical applications for controlling fungal infections.

Chemical Structure

Fungichromin
Fungichromin
CAS#6834-98-6

Theoretical Analysis

MedKoo Cat#: 461627

Name: Fungichromin

CAS#: 6834-98-6

Chemical Formula: C35H58O12

Exact Mass: 670.3928

Molecular Weight: 670.83

Elemental Analysis: C, 62.67; H, 8.72; O, 28.62

Price and Availability

Size Price Availability Quantity
10mg USD 1,250.00 2 Weeks
25mg USD 2,450.00 2 Weeks
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Related CAS #
Synonym
Fungichromin; Cogomycin; Lagosin; Pentamycin; 14-hydroxy Filipin; NSC 105388; NSC105388; NSC-105388; NSC 276732; NSC276732; NSC-276732; S 232; S-232; S232;
IUPAC/Chemical 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-((R)-1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
InChi Key
AGJUUQSLGVCRQA-SWOUQTJZSA-N
InChi Code
InChI=1S/C35H58O12/c1-4-5-11-16-29(41)32-30(42)20-26(38)18-24(36)17-25(37)19-27(39)21-31(43)34(45)33(44)22(2)14-12-9-7-6-8-10-13-15-28(40)23(3)47-35(32)46/h6-10,12-15,23-34,36-45H,4-5,11,16-21H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,22-14+/t23-,24+,25-,26+,27-,28+,29-,30+,31-,32-,33-,34-/m1/s1
SMILES Code
C/C1=C\C=C\C=C\C=C\C=C\[C@H](O)[C@@H](C)OC([C@H]([C@H](O)CCCCC)[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)[C@@H](O)[C@@H]1O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 670.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zeng Q, Huang H, Zhu J, Fang Z, Sun Q, Bao S. A new nematicidal compound produced by Streptomyces albogriseolus HA10002. Antonie Van Leeuwenhoek. 2013 May;103(5):1107-11. doi: 10.1007/s10482-013-9890-8. Epub 2013 Feb 27. PubMed PMID: 23444037; PubMed Central PMCID: PMC3621998. 2: An D, Wang X, Li J, Jiang S, Ma X, Zhang H, Shi H, Sun H, Ye L, Li J. The Activity of Fungichromin against the Formation of Candida albicans Biofilm. Biol Pharm Bull. 2016 Dec 1;39(12):1948-1954. Epub 2016 Sep 8. PubMed PMID: 27615430. 3: Xiong ZQ, Zhang ZP, Li JH, Wei SJ, Tu GQ. Characterization of Streptomyces padanus JAU4234, a producer of actinomycin X₂, fungichromin, and a new polyene macrolide antibiotic. Appl Environ Microbiol. 2012 Jan;78(2):589-92. doi: 10.1128/AEM.06561-11. Epub 2011 Nov 4. PubMed PMID: 22057866; PubMed Central PMCID: PMC3255745. 4: Human ZR, Moon K, Bae M, de Beer ZW, Cha S, Wingfield MJ, Slippers B, Oh DC, Venter SN. Antifungal Streptomyces spp. Associated with the Infructescences of Protea spp. in South Africa. Front Microbiol. 2016 Nov 2;7:1657. eCollection 2016. PubMed PMID: 27853450; PubMed Central PMCID: PMC5090004. 5: Shih HD, Liu YC, Hsu FL, Mulabagal V, Dodda R, Huang JW. Fungichromin: a substance from Streptomyces padanus with inhibitory effects on Rhizoctonia solani. J Agric Food Chem. 2003 Jan 1;51(1):95-9. PubMed PMID: 12502391. 6: Pandey RC, Guenther EC, Aszalos AA, Brajtburg J. Physicochemical and biological comparison of polyene macrolide antibiotics fungichromin, lagosin and cogomycin. J Antibiot (Tokyo). 1982 Aug;35(8):988-96. PubMed PMID: 7142017. 7: Cao Z, Yoshida R, Kinashi H, Arakawa K. Blockage of the early step of lankacidin biosynthesis caused a large production of pentamycin, citreodiol and epi-citreodiol in Streptomyces rochei. J Antibiot (Tokyo). 2015 May;68(5):328-33. doi: 10.1038/ja.2014.160. Epub 2014 Dec 3. PubMed PMID: 25464973. 8: Robison RS, Aszalos A, Kraemer N, Giannini SM. Production of fungichromin by streptoverticillium cinnamomeum subsp. cinnamomeum NRRL B-1285. J Antibiot (Tokyo). 1971 Apr;24(4):273. PubMed PMID: 5572757. 9: Rakotoniriana EF, Chataigné G, Raoelison G, Rabemanantsoa C, Munaut F, El Jaziri M, Urveg-Ratsimamanga S, Marchand-Brynaert J, Corbisier AM, Declerck S, Quetin-Leclercq J. Characterization of an endophytic whorl-forming Streptomyces from Catharanthus roseus stems producing polyene macrolide antibiotic. Can J Microbiol. 2012 May;58(5):617-27. doi: 10.1139/w2012-034. Epub 2012 Apr 23. PubMed PMID: 22524528. 10: Kranzler M, Syrowatka M, Leitsch D, Winnips C, Walochnik J. Pentamycin shows high efficacy against Trichomonas vaginalis. Int J Antimicrob Agents. 2015 Apr;45(4):434-7. doi: 10.1016/j.ijantimicag.2014.12.024. Epub 2015 Feb 2. PubMed PMID: 25703311. 11: Li Z, Rawlings BJ, Harrison PH, Vederas JC. Production of new polyene antibiotics by Streptomyces cellulosae after addition of ethyl (Z)-16-phenylhexadec-9-enoate. J Antibiot (Tokyo). 1989 Apr;42(4):577-84. PubMed PMID: 2722673. 12: Zygmunt WA. Intracellular Loss of Potassium in Candida albicans After Exposure to Polyene Antifungal Antibiotics. Appl Microbiol. 1966 Nov;14(6):953-6. PubMed PMID: 16349701; PubMed Central PMCID: PMC1058448. 13: LAMPEN JO, GILL JW, ARNOW PM, MAGANA-PLAZA I. INHIBITION OF THE PLEUROPNEUMONIA-LIKE ORGANISM MYCOPLASMA GALLISEPTICUM BY CERTAIN POLYENE ANTIFUNGAL ANTIBIOTICS. J Bacteriol. 1963 Nov;86:945-9. PubMed PMID: 14080805; PubMed Central PMCID: PMC278550. 14: Pandey RC, Kalita CC, Aszalos AA, Geoghegan R Jr, Garretson AL, Cook JC Jr, Rinehart KL Jr. Field desorption mass spectrometry in structural studies of polyene macrolide antibiotics: isolation and early identification of a pentaene macrolide antibiotic. Biomed Mass Spectrom. 1980 Mar;7(3):93-8. PubMed PMID: 6775705. 15: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Jun;32(5):331-88. doi: 10.1358/mf.2010.32.5.1520420. PubMed PMID: 20664824. 16: Frey Tirri B, Bitzer J, Geudelin B, Drewe J. Safety, tolerability and pharmacokinetics of intravaginal pentamycin. Chemotherapy. 2010;56(3):190-6. doi: 10.1159/000316329. Epub 2010 Jun 10. PubMed PMID: 20551634. 17: UMEZAWA S, TANAKA Y, OOKA M, SHIOTSU S. A new antifungal antibiotic, pentamycin. J Antibiot (Tokyo). 1958 Jan;11(1):26-9. PubMed PMID: 13525250. 18: ARORA HR. A STUDY ON THE EFFECTS OF PENTAMYCIN AND PIMARICIN, TWO POLYENE ANTIFUNGAL ANTIBIOTICS ON THE GUINEA PIG HEART. Med Pharmacol Exp Int J Exp Med. 1965;12:239-44. PubMed PMID: 14317086. 19: Braga A. [Preliminary clinical trials of pentamycin]. Clin Ter. 1980 Jan 31;92(2):137-42. Italian. PubMed PMID: 6993089. 20: Cóias R, Galego L, Barahona I, Rodrigues-Pousada C. Destabilization of tubulin mRNA during heat shock in Tetrahymena pyriformis. Eur J Biochem. 1988 Aug 15;175(3):467-74. PubMed PMID: 3137027.