U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H58O12
Molecular Weight 670.8278
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAMYCIN

SMILES

[H][C@@]1([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](O)\C(C)=C\C=C\C=C\C=C\C=C\[C@H](O)[C@@H](C)OC1=O

InChI

InChIKey=AGJUUQSLGVCRQA-SWOUQTJZSA-N
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

HIDE SMILES / InChI

Molecular Formula C35H58O12
Molecular Weight 670.8278
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://print.ispub.com/api/0/ispub-article/5140 and http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=193796

Pentamycin, also called fungichromin, is a macrolide antibiotic. Pentamycin is a polyene antifungal antibiotic obtained from Streptomyces pentaticus. Pentamycin is a unique treatment for all types of infectious vaginitis, a common condition affecting up to 10% of all women each year whose treatment generates more than 100 million prescriptions per year across Europe and North America. Pentamycin has been shown to be effective against all pathogens which cause infectious vaginitis without negative effect on critical components of the vagina ’s natural flora. Pentamycin is not absorbed into the bloodstream and is well tolerated. In addition, its spectrum includes activity against pathogens resistant to current standard treatment. Pentamycin under the brand name FemiFec is approved in Switzerland for the treatment of vaginitis. FemiFect is the first broad-spectrum antibiotic approved to treat all three of the most common infections known to cause vaginitis: bacteria, fungi and protozoa. Due to the specific molecular structure of pentamycin, FemiFect has several unique properties that clearly differentiate it from existing products: Broad spectrum: Effective against all major pathogens involved in vaginitis; Safety profile: No systemic absorption due to a large molecule size; Resistance: No development of resistance reported to date.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Trichomonas vaginalis growth
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FemiFect

Approved Use

FemiFect (pentamycin) is the first broad-spectrum antibiotic approved to treat all three of the most common infections known to cause vaginitis: bacteria, fungi and protozoa.

Launch Date

2009
PubMed

PubMed

TitleDatePubMed
HM17, a new polyene antifungal antibiotic produced by a new strain of Spirillospora.
1994 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: vaginal tablet
Intravaginally (3-100 mg) daily for 6 days.
Route of Administration: Vaginal
In Vitro Use Guide
Treatment with 15 ug/mL (22 uM) of Pentamycin for 1 h or with ≥1 ug/mL (≥1.5 uM) for 24 h totally eradicated trichomonads
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:25:49 GMT 2023
Edited
by admin
on Sat Dec 16 01:25:49 GMT 2023
Record UNII
1JB340D58S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTAMYCIN
JAN   WHO-DD  
Common Name English
PRURI-EX
Brand Name English
ANTIBIOTIC A 246
Code English
PENTAMYCIN [JAN]
Common Name English
FUNGCHROMIN
MI  
Common Name English
LAGOSIN
Common Name English
ANTIBIOTIC A-246
Code English
FUNGCHROMIN [MI]
Common Name English
FEMIFECT
Brand Name English
CANTRICIN
Common Name English
COGOMYCIN
Common Name English
Pentamycin [WHO-DD]
Common Name English
(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-DIMETHYLOXACYCLOOCTACOSA-17,19,21,23,25-PENTAEN-2-ONE
Common Name English
NSC-105388
Code English
NSC-276732
Code English
Classification Tree Code System Code
WHO-ATC G01AA11
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
WHO-VATC QG01AA11
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
Code System Code Type Description
SMS_ID
100000079757
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
EVMPD
SUB14796MIG
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
DRUG CENTRAL
3254
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
FDA UNII
1JB340D58S
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID4046866
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
ECHA (EC/EINECS)
229-913-4
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
PUBCHEM
5282200
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
DRUG BANK
DB13571
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
WIKIPEDIA
PENTAMYCIN
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
NSC
105388
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
NSC
276732
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
MESH
C011827
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY
CAS
6834-98-6
Created by admin on Sat Dec 16 01:25:50 GMT 2023 , Edited by admin on Sat Dec 16 01:25:50 GMT 2023
PRIMARY