Allopurinol

Modify Date: 2024-01-02 12:43:39

Allopurinol Structure
Allopurinol structure
 Common Name Allopurinol
CAS Number 315-30-0 Molecular Weight 136.111
Density 1.7±0.1 g/cm3 Boiling Point 290.8ºC at 760 mmHg
Molecular Formula C5H4N4O Melting Point 350 ºC
MSDS Chinese USA Flash Point 129.7ºC
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Allopurinol


Allopurinol (Zyloprim) is a xanthine oxidase inhibitor with an IC50 of 7.82±0.12 μM.Target: XAOAllopurinol (Zyloprim, and generics) is a drug used primarily to treat hyperuricemia (excess uric acid in blood plasma) and its complications, including chronic gout. It is a xanthine oxidase inhibitor which is administered orally. A common misconception is that allopurinol is metabolized by its target, xanthine oxidase, but this action is principally carried out by Aldehyde oxidase. The active metabolite of allopurinol is oxypurinol, which is also an inhibitor of xanthine oxidase. Allopurinol is almost completely metabolized to oxypurinol within two hours of oral administration, whereas oxypurinol is slowly excreted by the kidneys over 18–30 hours. For this reason, oxypurinol is believed responsible for the majority of allopurinol's effect.Allopurinol is a purine analog; it is a structural isomer of hypoxanthine (a naturally occurring purine in the body) and is an inhibitor of the enzyme xanthine oxidase. In addition to blocking uric acid production, inhibition of xanthine oxidase causes an increase in hypoxanthine and xanthine. While xanthine cannot be converted to purine ribotides, hypoxanthine can be salvaged to the purine ribotides adenosine and guanosine monophosphates. Increased levels of these ribotides may cause feedback inhibition of amidophosphoribosyl transferase, the first and rate-limiting enzyme of purine biosynthesis. Allopurinol, therefore, decreases uric acid formation and may also inhibit purine synthesis.

 Names

Name allopurinol
Synonym More Synonyms

 Allopurinol Biological Activity

Description Allopurinol (Zyloprim) is a xanthine oxidase inhibitor with an IC50 of 7.82±0.12 μM.Target: XAOAllopurinol (Zyloprim, and generics) is a drug used primarily to treat hyperuricemia (excess uric acid in blood plasma) and its complications, including chronic gout. It is a xanthine oxidase inhibitor which is administered orally. A common misconception is that allopurinol is metabolized by its target, xanthine oxidase, but this action is principally carried out by Aldehyde oxidase. The active metabolite of allopurinol is oxypurinol, which is also an inhibitor of xanthine oxidase. Allopurinol is almost completely metabolized to oxypurinol within two hours of oral administration, whereas oxypurinol is slowly excreted by the kidneys over 18–30 hours. For this reason, oxypurinol is believed responsible for the majority of allopurinol's effect.Allopurinol is a purine analog; it is a structural isomer of hypoxanthine (a naturally occurring purine in the body) and is an inhibitor of the enzyme xanthine oxidase. In addition to blocking uric acid production, inhibition of xanthine oxidase causes an increase in hypoxanthine and xanthine. While xanthine cannot be converted to purine ribotides, hypoxanthine can be salvaged to the purine ribotides adenosine and guanosine monophosphates. Increased levels of these ribotides may cause feedback inhibition of amidophosphoribosyl transferase, the first and rate-limiting enzyme of purine biosynthesis. Allopurinol, therefore, decreases uric acid formation and may also inhibit purine synthesis.
Related Catalog
References

[1]. Pacher P, et al. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114.

[2]. Reiter S, et al. Demonstration of a combined deficiency of xanthine oxidase and aldehyde oxidase in xanthinuric patients not forming oxipurinol. Clin Chim Acta. 1990 Mar 15;187(3):221-34.

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Boiling Point 290.8ºC at 760 mmHg
Melting Point 350 ºC
Molecular Formula C5H4N4O
Molecular Weight 136.111
Flash Point 129.7ºC
Exact Mass 136.038513
PSA 74.43000
LogP -1.46
Index of Refraction 1.816
Water Solubility 0.35 g/L (25 ºC)

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UR0785000
CHEMICAL NAME :
H-Pyrazolo(3,4-d)pyrimidin-4-ol
CAS REGISTRY NUMBER :
315-30-0
LAST UPDATED :
199803
DATA ITEMS CITED :
19
MOLECULAR FORMULA :
C5-H4-N4-O
MOLECULAR WEIGHT :
136.13
WISWESSER LINE NOTATION :
T56 BMN GN INJ FQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
42 mg/kg/7D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 76,47,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
120 mg/kg/4W-I
TOXIC EFFECTS :
Blood - other changes Skin and Appendages - dermatitis, allergic (after systemic exposure) Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
CEDEDE Clinical and Experimental Dermatology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1976- Volume(issue)/page/year: 19,243,1994
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
88 mg/kg/22D-I
TOXIC EFFECTS :
Blood - leukopenia
REFERENCE :
ARDIAO Annals of the Rheumatic Diseases. (British Medical Journal, Box 560B, Kennebunkport, ME 04041) V.1- 1939- Volume(issue)/page/year: 40,245,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
21429 ug/kg/5D-I
TOXIC EFFECTS :
Behavioral - muscle weakness Liver - jaundice, other or unclassified Blood - thrombocytopenia
REFERENCE :
ARDIAO Annals of the Rheumatic Diseases. (British Medical Journal, Box 560B, Kennebunkport, ME 04041) V.1- 1939- Volume(issue)/page/year: 40,245,1981
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 7,735,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
900 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ADTEAS Advances in Teratology. (New York, NY) V.1-5, 1966-72. Discontinued. Volume(issue)/page/year: 3,181,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
78 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 7,735,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
214 mg/kg
TOXIC EFFECTS :
Behavioral - food intake (animal) Behavioral - fluid intake Behavioral - ataxia
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 64,108,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
298 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 23,715,1981
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 7,735,1973 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
300 mg/kg/3D-I
TOXIC EFFECTS :
Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 9,343,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg/10D-I
TOXIC EFFECTS :
Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 9,343,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
300 mg/kg/3D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Kidney, Ureter, Bladder - changes in bladder weight Biochemical - Metabolism (Intermediary) - xanthine, purine or nucleotides including urate
REFERENCE :
JJPAAZ Japanese Journal of Pharmacology. (Japanese Pharmacological Soc., c/o Dept. of Pharmacology, Faculty of Medicine, Kyoto Univ., Sakyo-ku, Kyoto 606, Japan) V.1- 1951- Volume(issue)/page/year: 45,271,1987 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
50 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
JJPAAZ Japanese Journal of Pharmacology. (Japanese Pharmacological Soc., c/o Dept. of Pharmacology, Faculty of Medicine, Kyoto Univ., Sakyo-ku, Kyoto 606, Japan) V.1- 1951- Volume(issue)/page/year: 22,201,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
JJPAAZ Japanese Journal of Pharmacology. (Japanese Pharmacological Soc., c/o Dept. of Pharmacology, Faculty of Medicine, Kyoto Univ., Sakyo-ku, Kyoto 606, Japan) V.1- 1951- Volume(issue)/page/year: 22,201,1972 *** REVIEWS *** TOXICOLOGY REVIEW INTEAG Internist. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1960- Volume(issue)/page/year: 15,7,1974 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4802 No. of Facilities: 94 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 1456 (estimated) No. of Female Employees: 840 (estimated)

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H317
Precautionary Statements Missing Phrase - N15.00950417-P280
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic
Risk Phrases R25;R36/37/38;R43
Safety Phrases S28-S36/37-S45-S36/37/39-S26-S24
RIDADR UN 2811 6.1/PG 3
WGK Germany 2
RTECS UR0785000
Packaging Group III
Hazard Class 6.1
HS Code 2933990090

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

Urosin
Urbol
7H-Pyrazolo[3,4-d]pyrimidin-4-ol
Apurol
Pural
1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
Anoprolin
HPP
Sigapurol
allopurinal
aloral
T56 BMN GN INJ FQ
Epidropal
Apurin
4-HPP
4-Hydroxypyrazolo[3,4-d]pyrimidine
Zyloprim
Isopurinol
AL-100
Takanarumin
1H-Pyrazolo[3,4-d]pyrimidin-4-ol
4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,7-dihydro-
Caplenal
Allopurinol
Remid
MFCD00599413
Bleminol
EINECS 206-250-9
Allopurin
Foligan
Anzief
1H-Pyrazolo(3,4-d)pyrimidin-4-ol (4-Hydroxypyrazolo(3,4-d)pyrimidine
Hexanurat
Adenock
Cellidrin
Hexanuret
Zyloric (Trade name)
Zyloric
1H-Pyrazolo[3,4-d]pyrimidin-4(5H)-one
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Related Compounds: More...
allopurinol
291279-53-3
Allopurinol-d2
916979-34-5
Allopurinolsodium
17795-21-0
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16220-07-8
5-Methyl-allopurinol
17840-75-4
5-Methyl-allopurinol
66074-29-1
Allopurinol Impurity 7
16617-46-2
Allopurinol Impurity E
31055-19-3
ALLOPURINOL IMPURITY F
321571-07-7
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