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Substance Name: Allopurinol [USAN:USP:INN:BAN:JAN]
RN: 315-30-0
UNII: 63CZ7GJN5I
InChIKey: OFCNXPDARWKPPY-UHFFFAOYSA-N

Note

  • A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.

Molecular Formula

  • C5-H4-N4-O

Molecular Weight

  • 136.1136
 

Classification Codes

  • Antimetabolites
  • Antioxidants
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Free Radical Scavengers
  • Gout Suppressants
  • Human Data
  • Noxae
  • Reproductive Effect
  • Xanthine Oxidase Inhibitor

Names and Synonyms

Name of Substance

  • Allopurinol
  • Allopurinol [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Allopurinol

Synonyms

  • 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidin-4-one
  • 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one
  • 1H-Pyrazolo(3,4-d)pyrimidin-4-ol
  • 4'-Hydroxypyrazolol(3,4-d)pyrimidine
  • 4-HPP
  • 4-Hydroxy-1H-pyrazolo(3,4-d)pyrimidine
  • 4-Hydroxy-3,4-pyrazolopyrimidine
  • 4-Hydroxypyrazolo(3,4-d)pyrimidine
  • 4-Hydroxypyrazolopyrimidine
  • 4-Hydroxypyrazolyl(3,4-d)pyrimidine
  • 4H-Pyrazolo(3,4-d)pyrimidin-4-one
  • 4H-Pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-
  • Adenock
  • Ailural
  • AL-100
  • Allo-Puren
  • Allopur
  • Allopurinol
  • Allopurinol(I)
  • Allopurinolum
  • Allopurinolum [INN-Latin]
  • Allozym
  • Allural
  • Alopurinol
  • Alopurinol [INN-Spanish]
  • Aloral
  • Alositol
  • Aluline
  • Anoprolin
  • Anzief
  • Apulonga
  • Apurin
  • Apurol
  • ATH008
  • Atisuril
  • B. W. 56-158
  • Bleminol
  • Bloxanth
  • BW 56-158
  • Caplenal
  • CCRIS 626
  • Cellidrin
  • Cosuric
  • Dabrosin
  • Dabroson
  • Dura Al
  • EINECS 206-250-9
  • Embarin
  • Epidropal
  • Epuric
  • Foligan
  • Geapur
  • Gichtex
  • Gotax
  • Hamarin
  • Hexanuret
  • HPP
  • HSDB 3004
  • Ketanrift
  • Ketobun-A
  • Ledopur
  • Lopurin
  • Lysuron
  • Milurit
  • Miniplanor
  • Monarch
  • Nektrohan
  • NSC 101655
  • NSC 1390
  • NSC-1390
  • Progout
  • Remid
  • Riball
  • Suspendol
  • Takanarumin
  • UNII-63CZ7GJN5I
  • Urbol
  • Uricemil
  • Uriprim
  • Uripurinol
  • Urobenyl
  • Urolit
  • Urosin
  • Urtias
  • Urtias 100
  • Xanturat
  • Zyloprim
  • Zyloric

Systematic Names

  • 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidin-4-one (9CI)
  • 1H-Pyrazolo(3,4-d)pyrimidin-4-ol
  • 4H-Pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-
  • Allopurinol

Registry Numbers

CAS Registry Number

  • 315-30-0

FDA UNII

  • 63CZ7GJN5I

Other Registry Numbers

  • 184856-42-6
  • 22767-92-6
  • 39464-14-7

System Generated Number

  • 0000315300

Structure Descriptors

InChI

1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

InChIKey

OFCNXPDARWKPPY-UHFFFAOYSA-N

Smiles

c12c([nH]cnc1=O)[nH]nc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 21429ug/kg/5D (21.429mg/kg) BLOOD: THROMBOCYTOPENIA

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BEHAVIORAL: MUSCLE WEAKNESS
Annals of the Rheumatic Diseases. Vol. 40, Pg. 245, 1981.
man TDLo oral 120mg/kg/4W-I (120mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

BLOOD: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Clinical and Experimental Dermatology. Vol. 19, Pg. 243, 1994.
mouse LD50 intraperitoneal 214mg/kg (214mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: FLUID INTAKE

BEHAVIORAL: ATAXIA
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 108, 1968.
mouse LD50 oral 78mg/kg (78mg/kg)   Pharmaceutical Chemistry Journal Vol. 7, Pg. 735, 1973.
mouse LD50 subcutaneous 298mg/kg (298mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 715, 1981.
rabbit LD oral > 100mg/kg (100mg/kg)   Pharmaceutical Chemistry Journal Vol. 7, Pg. 735, 1973.
rat LD oral > 500mg/kg (500mg/kg)   Pharmaceutical Chemistry Journal Vol. 7, Pg. 735, 1973.
rat LD50 intraperitoneal 900mg/kg (900mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LD50 subcutaneous 2450mg/kg (2450mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 763, 1969.
women LDLo oral 88mg/kg/22D-I (88mg/kg) BLOOD: LEUKOPENIA Annals of the Rheumatic Diseases. Vol. 40, Pg. 245, 1981.
women TDLo oral 42mg/kg/7D-I (42mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
American Journal of Medicine. Vol. 76, Pg. 47, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 350 deg C   EXP
log P (octanol-water) -0.55 (none)   EXP
Water Solubility 569 mg/L 25 EXP
Vapor Pressure 4.73E-06 mm Hg 25 EST
Henry's Law Constant 2.03E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.00E-10 cm3/molecule-sec 25 EST

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