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Substance Name: Amphotericin B [USP:INN:JAN]
RN: 1397-89-3
UNII: 7XU7A7DROE
InChIKey: APKFDSVGJQXUKY-INPOYWNPSA-N

Note

  • Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.

Molecular Formula

  • C47-H73-N-O17

Molecular Weight

  • 924.0837
 

Classification Codes

  • Amebicides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal
  • Antifungal Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Amphotericin B
  • Amphotericin B [USP:INN:JAN]

MeSH Heading

  • Amphotericin B

Synonyms

  • (1R-(1R*,3S*,5R*,6R*,9R*,11R*,15S*,16R*,17R*,18S*,19E,21E,23E,25E,27E,29E,31E,33R*,35S*,36R*,37S*))-33-((3-Amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
  • 14,39-Dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,2 7,29,31-heptaene-36-carboxylic acid, 33-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-(1R-(1R*,3S*,5R*,6R*,9R*,11R*,15S*,16R*,17R*,18S*,19E,21E,23E, 25E-27E,29E,31E,33R*,35S*,36R*,37S*))-
  • 5-18-10-00525 (Beilstein Handbook Reference)
  • Abelcet
  • Abelecet
  • AI3-26528
  • Ambisome
  • Amfotericina B
  • Amfotericina B [INN-Spanish]
  • Ampho-Moronal
  • Amphocil
  • Amphocin
  • Amphotec
  • Amphotericin B
  • Amphotericine B
  • Amphotericine B [INN-French]
  • Amphotericinum B
  • Amphotericinum B [INN-Latin]
  • Amphozone
  • Anfotericine B
  • BRN 0078342
  • CCRIS 5963
  • EINECS 215-742-2
  • Fungilin
  • Fungizone
  • Halizon
  • HSDB 3008
  • IAB
  • Mysteclin-F
  • NS 718
  • NSC 527017
  • Tegopen
  • UNII-7XU7A7DROE

Systematic Name

  • Amphotericin B

Mixture Names

  • Mysteclin-F
  • Talsutin

Registry Numbers

CAS Registry Number

  • 1397-89-3

FDA UNII

  • 7XU7A7DROE

Other Registry Numbers

  • 1407-52-9
  • 30782-62-8
  • 54482-28-9
  • 8055-20-7

System Generated Number

  • 0001397893

Structure Descriptors

InChI

1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

InChIKey

APKFDSVGJQXUKY-INPOYWNPSA-N

Smiles

C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 6mg/kg (6mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES Biokhimiya Vol. 43, Pg. 2043, 1978.
infant TDLo intravenous 15mg/kg/4D-I (15mg/kg)   Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 371, 1990.
infant TDLo intravenous 15mg/kg/4D-I (15mg/kg)   Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 371, 1990.
man LDLo intravenous 164ug/kg/5H-I (0.164mg/kg) CARDIAC: OTHER CHANGES Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 547, 1983.
mouse LD unreported > 50mg/kg (50mg/kg)   Journal of Antibiotics. Vol. 24, Pg. 561, 1971.
mouse LD12 oral 280mg/kg (280mg/kg)   British UK Patent Application. Vol. #2067993,
mouse LD50 intramuscular > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
mouse LD50 intraperitoneal 27740ug/kg (27.74mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 1200ug/kg (1.2mg/kg)   Pharmacy International. Vol. 6, Pg. 164, 1985.
rabbit LDLo intravenous 5mg/kg (5mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics Annual. Vol. 5, Pg. 53, 1957/1958.
rat LD50 intramuscular > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
rat LD50 intravenous 1600ug/kg (1.6mg/kg)   Journal of Antimicrobial Chemotherapy. Vol. 28(Suppl,
rat LD50 oral > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976.
women LDLo intravenous 22mg/kg/4D-I (22mg/kg) BLOOD: LEUKOPENIA Southern Medical Journal. Vol. 76, Pg. 409, 1983.
women TDLo intravenous 20ug/kg (0.02mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES New England Journal of Medicine. Vol. 315, Pg. 836, 1986.
women TDLo intravenous 1mg/kg/1H-C (1mg/kg) CARDIAC: PULSE RATE Lancet. Vol. 341, Pg. 372, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.800 (none)   EST
Water Solubility 750 mg/L 28 EXP
Atmospheric OH Rate Constant 6.48E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.