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Details

Stereochemistry UNKNOWN
Molecular Formula 2C55H103N3O17.H2O4S
Molecular Weight 2254.911
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 40
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRIMYCIN SULFATE

SMILES

OS(O)(=O)=O.CCCCC1C(O)C(C)CCC(O)CCCC(O)CCCC(O)\C(C)=C\C(OC2OC(CO)C(O)C2O)C(O)CC(O)CC(O)CC(O)CC(O)CCCC\C(C)=C\C(C)C(OC1=O)C(C)C(O)CCCNC(N)=N.CCCCC3C(O)C(C)CCC(O)CCCC(O)CCCC(O)\C(C)=C\C(OC4OC(CO)C(O)C4O)C(O)CC(O)CC(O)CC(O)CC(O)CCCC\C(C)=C\C(C)C(OC3=O)C(C)C(O)CCCNC(N)=N

InChI

InChIKey=BZARQXGRENRAGM-YQALYVIGSA-N
InChI=1S/2C55H103N3O17.H2O4S/c2*1-7-8-19-43-49(69)33(3)22-23-38(61)17-11-16-37(60)18-12-20-44(66)34(4)26-47(73-54-51(71)50(70)48(31-59)74-54)46(68)30-42(65)29-41(64)28-40(63)27-39(62)15-10-9-14-32(2)25-35(5)52(75-53(43)72)36(6)45(67)21-13-24-58-55(56)57;1-5(2,3)4/h2*25-26,33,35-52,54,59-71H,7-24,27-31H2,1-6H3,(H4,56,57,58);(H2,1,2,3,4)/b2*32-25+,34-26+;

HIDE SMILES / InChI
Primycin is a topical antibiotic developed in Hungary for the local treatment of certain superficial and deep infections of the skin and subcutaneous tissue. Primycin is a complex of macrocyclic antibiotics comprising 20 compounds. Primycin possesses good in vitro activity against Staphylococcus aureus and coagulase-negative staphylococci, but its activity against Sirepiococctts pyogenes and enterococci is moderate. It is active against Micrococcus and Bacillus spp. but is inactive against Corynebacterium spp. It is inactive against Enterofojcterwceae and Pseudomonas aeruginosa, yeasts, and dermatophytes. The median lethal dose in the mouse is greater than 3,000 mg/kg of body weight orally and 56 mg/kg intraperitoneally. No skin lesions have been observed after chronic cutaneous applications (90 days) in the rabbit.

Originator

Sources: Nature (1954), 174, (4441), 1105-6.

Approval Year

PubMed

PubMed

TitleDatePubMed
Complex formation between primycin and ergosterol: entropy-driven initiation of modification of the fungal plasma membrane structure.
2012 Apr
Effect of primycin on growth-arrested cultures and cell integrity of Staphylococcus aureus.
2017 Jun 1
Patents
Name Type Language
PRIMYCIN SULFATE
MI   WHO-DD  
Common Name English
PRIMYCIN SULFATE [MI]
Common Name English
Primycin sulfate [WHO-DD]
Common Name English
PRIMYCIN SULPHATE
Common Name English
GUANIDINE, N-(5-(19-(.ALPHA.-D-ARABINOFURANOSYLOXY)-35-BUTYL-10,12,14,16,18,22,26,30,34-NONAHYDROXY-3,5,21,33-TETRAMETHYL-36-OXOOXACYCLOHEXATRIACONTA-4,20-DIEN-2-YL)-4-HYDROXYHEXYL)-, SULFATE (2:1)
Systematic Name English
DEBRYCIN SULFATE
Common Name English
PRIMYCIN A1, SULFATE (2:1) SALT
Common Name English
Code System Code Type Description
CAS
30003-49-7
Created by admin on Sat Dec 16 10:20:49 GMT 2023 , Edited by admin on Sat Dec 16 10:20:49 GMT 2023
PRIMARY
MERCK INDEX
m9138
Created by admin on Sat Dec 16 10:20:49 GMT 2023 , Edited by admin on Sat Dec 16 10:20:49 GMT 2023
PRIMARY
FDA UNII
V303FVN95C
Created by admin on Sat Dec 16 10:20:49 GMT 2023 , Edited by admin on Sat Dec 16 10:20:49 GMT 2023
PRIMARY
CAS
128644-47-3
Created by admin on Sat Dec 16 10:20:49 GMT 2023 , Edited by admin on Sat Dec 16 10:20:49 GMT 2023
NO STRUCTURE GIVEN
PUBCHEM
118984400
Created by admin on Sat Dec 16 10:20:49 GMT 2023 , Edited by admin on Sat Dec 16 10:20:49 GMT 2023
PRIMARY