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Substance Name: Puromycin [USAN:INN:BAN]
RN: 53-79-2
UNII: 4A6ZS6Q2CL
InChIKey: RXWNCPJZOCPEPQ-NVWDDTSBSA-N

Note

  • A cinnamamido ADENOSINE found in STREPTOMYCES alboniger. It inhibits protein synthesis by binding to RNA. It is an antineoplastic and antitrypanosomal agent and is used in research as an inhibitor of protein synthesis.

Molecular Formula

  • C22-H29-N7-O5

Molecular Weight

  • 471.5151
 

Classification Codes

  • Anti-Infective Agents
  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Antiparasitic Agents
  • Antiprotozoal (Trypanosoma)
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Noxae
  • Protein Synthesis Inhibitors
  • Reproductive Effect
  • Trypanocidal Agents
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Names and Synonyms

Name of Substance

  • Puromycin
  • Puromycin [USAN:INN:BAN]

MeSH Heading

  • Puromycin

Synonyms

  • (S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyladenosine
  • 3'-(L-alpha-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine
  • 3123L
  • 6-Dimethylamino-9-(3'-(p-methoxy-L-phenylalanylamino)-beta-D-ribofuranosyl)-purine
  • Achromycin
  • Achromycin (purine derivative)
  • Adenosine, 3'-((2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-, (S)-
  • CL 13,900
  • CL 13900
  • CL 16536
  • NSC-3055
  • P 638
  • P-638
  • Puromicina
  • Puromicina [INN-Spanish]
  • Puromycin
  • Puromycine
  • Puromycine [INN-French]
  • Puromycinum
  • Puromycinum [INN-Latin]
  • Stillomycin
  • Stylomycin
  • UNII-4A6ZS6Q2CL

Systematic Names

  • Adenosine, 3'-(((2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-
  • Adenosine, 3'-((2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-, (S)-
  • Adenosine, 3'-(alpha-amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyl-, L-

Registry Numbers

CAS Registry Number

  • 53-79-2

FDA UNII

  • 4A6ZS6Q2CL

Related Registry Number

  • 58-58-2 (di-hydrochloride)

System Generated Number

  • 0000053792

Structure Descriptors

InChI

1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1

InChIKey

RXWNCPJZOCPEPQ-NVWDDTSBSA-N

Smiles

CN(C)c1c2c(ncn1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)NC(=O)[C@H](Cc4ccc(cc4)OC)N)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 25mg/kg (25mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 302, 1981.
mouse LD50 intravenous 15mg/kg (15mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 302, 1981.
mouse LD50 oral 20mg/kg (20mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 302, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 175.5-177 deg C   EXP
log P (octanol-water) 0.03 (none)   EXP
Water Solubility 50.3 mg/L 25 EST
Vapor Pressure 1.03E-22 mm Hg 25 EST
Henry's Law Constant 5.94E-31 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.16E-10 cm3/molecule-sec 25 EST

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