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Home> Encyclopedia >   /  Urinary System Agents  /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Organic Intermediate  /  Organic Intermediates
Allopurinol structure
Allopurinol structure

Allopurinol

Iupac Name:1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
CAS No.:315-30-0
Molecular Weight:136.11146
Introduction: Odorless tasteless white microcrystalline powder.
1. Names and Identifiers
1.1 Name
Allopurinol
1.2 Synonyms

1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE(ALLOPURINOL) 1H-Pyrazolo[3,4-d]pyrimidin-4-ol 4-Hydroxypyrazolo[3,4-d]pyrimidine 4-Oxopyrazolo[3,4-d]pyrimidine Allopurinol ALLOPURINOL(P) ALLOPURINOL,USP AllopurinolBp2001 Hydroxypyrazolodpyrimidine NSC 101655 pyrazolo(3,4-d)pyrimidin-1-ol

1.3 CAS No.
315-30-0
1.4 CID
135401907
1.5 EINECS(EC#)
206-250-9
1.6 Molecular Formula
C5H4N4O (isomer)
1.7 Inchi
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
1.8 InChkey
OFCNXPDARWKPPY-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=NNC2=C1C(=O)NC=N2
1.10 Isomers Smiles
C1=NNC2=C1C(=O)NC=N2
2. Properties
3.1 Density
1.89
3.2 Melting Point
350℃
3.3 Boiling Point
290.8 °C at 760 mmHg
3.4 Vapour
1.17X10-8 mm Hg at 25 °C (est)
3.5 Refractive Index
1.816
3.6 Flash Point
129.7 °C
3.7 Appearance
White to Off-White Solid
3.8 Chemical Properties
White to Off-White Solid
3.9 Color/Form
Powder
3.10 Decomposition
When heated to decomposition it emits toxic fumes of oxides of /nitric oxide/.
3.11 Odor
SLIGHT
3.12 pKa
10.2(at 25℃)
3.13 Solubility
1 M NaOH: soluble50mg/mL, clear to very slightly hazy, colorless to faintly yellow
3.14 Spectral Properties
MASS: 107183 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
UV Maximum absorption (O.1N Sodium hydroxide): 257 nm (molar extinction coefficient = 7200 g-moles/L); (0.1N hydrogen chloride): 250 nm (molar extinction coefficient = 7600 g-moles/L); (methanol): 252 nm (molar extinction coefficient = 7600 g-moles/L).
3.15 Stability
Stable under normal temperatures and pressures.
3.16 StorageTemp
Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.
3.17 Water Solubility
0.35 g/L (25 °C) in water
3. Use and Manufacturing
4.1 Fire Hazard
Flash point data for Allopurinol are not available; however, Allopurinol is probably combustible.
4.2 General Description
Odorless tasteless white microcrystalline powder.
4.3 Safety Profile
Human poison byingestion. Poison experimentally byintraperitoneal and subcutaneous routes. Anexperimental teratogen. Human systemiceffects by ingestion: blood leukopenia,dermatitis, jaundice, muscle weakness,thrombocytopenia. When heated todecomposition it emits toxic fumes of NOx.An FDA proprietary drug used as a xanthineoxidase inhibitor.
4.4 Storage
Ambient temperatures.
4.5 Usage
Allopurinol does not reduce serum uric acid levels by increasing renal uric acid excretion; instead it lowers plasma urate levels by inhibiting the final steps in uric acid biosynthesis. Uric acid in humans is formed primarily by xanthine oxidase-catalyzed oxidation of hypoxanthine and xanthine to uric acid. Allopurinol (8) and its primary metabolite, alloxanthine (9) [CAS: 2465-59-0], are inhibitors of xanthine oxidase. Inhibition of the last two steps in uric acid biosynthesis by blocking xanthine oxidase reduces the plasma concentration and urinary excretion of uric acid and increases the plasma levels and renal excretion of the more soluble oxypurine precursors. Normally, in humans the urinary purine content is almost solely uric acid; treatment with allopurinol results in the urinary excretion of hypoxanthine, xanthine, and uric acid, each with its independent solubility. Lowering the uric acid concentration in plasma below its limit of solubility facilitates the dissolution of uric acid deposits. The effectiveness of allopurinol in the treatment of gout and hyperuricemia that results from hematogical disorders and antineoplastic therapy has been demonstrated.
4. Safety and Handling
5.1 Hazard Codes
T
5.1 Risk Statements
R25;R36/37/38;R43
5.2 Safety Statements
S24;S26;S36/37/39;S45
5.3 HazardClass
6.1
5.4 PackingGroup
III
5.5 Transport
UN 2811
5.6 Cleanup Methods
Wipe up spillage or collect spillage using a high- efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
5.7 DisposalMethods
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
5.8 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including allopurinol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
5.9 Fire Fighting Procedures
Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.
As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
5.10 Formulations/Preparations
Allopurinol Preparations: (AHFS, 2009) Allopurinol Preparations: (AHFS, 2009) Route Dosage Form Strength Brand (Manufacturer) Oral Tablets 100 mg Zyloprim; (Prometheus) Oral Tablets 300 mg Zyloprim; (Prometheus) Parenteral Injection 500 mg of allopurinol Aloprim; (Nabi)
Oral Tablets, 100 mg, Lopurin (scored), Boots; Zyloprim (with povidone; scored), Burroughs Wellcome; 300 mg, Lopurin (scored), Boots; Zyloprim (with povidone; scored), Burroughs Wellcome.
Tablets, 100 and 300 mg
5.11 Octanol/Water Partition Coefficient
log Kow = -0.55
5.12 Other Preventative Measures
This material is assumed to be combustible. As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.
As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.
/Use/ safety glasses or goggles /and/ protect exposed skin.
5.13 Protective Equipment and Clothing
Engineering controls such as exhaust ventilation are recommended.
Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.
5.14 Reactivities and Incompatibilities
/Incompatible with/ strong oxidizing agents.
Allopurinol sodium injection has been reported to be incompatible with various drugs (eg, sodium bicarbonate), but the compatibility depends on several factors (eg, concentrations of the drugs, resulting pH, temperature). Specialized references should be consulted for specific compatibility information.
Drugs that are physically incompatible in solution with (allopurinol sodium) for Injection Amikacin sulfate, Hydroxyzine HCl, Amphoterecin, BIdarubicin HCl, CarmustineImipenem-cilastatin sodium, Cefotaxime sodium, Mechlorethamine HCl, Chlorpromazine HCl, Meperidine HCl, Cimetidine HCl, Metoclopramide HCl, Clindamycin phosphate, Methylprednisolone sodium succinate, Cytarabine, Minocycline HCl Dacarbazine, Nalbuphine HCl, Daunorubicin HCl, Netilmicin sulfate, Diphenhydramine HCl, Ondansetron HCl, Doxorubicin HCl, Prochlorperazine edisylate, Doxycycline hyclate, Promethazine HCl, Droperidol, Sodium bicarbonate, Floxuridine, Streptozocin, Gentamicin sulfate,Tobramycin sulfate, Haloperidol lactate, and Vinorelbine tartrate
5.15 Report

Reported in EPA TSCA Inventory.

5.16 Safety

Human poison by ingestion. Poison experimentally by intraperitoneal and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: blood leukopenia, dermatitis, jaundice, muscle weakness, thrombocytopenia. When heated to decomposition it emits toxic fumes of NOx. An FDA proprietary drug used as a xanthine oxidase inhibitor.
Hazard Codes?of Allopurinol (CAS NO.315-30-0):?ToxicT,IrritantXi,HarmfulXn
Risk Statements: 25-43-36/37/38-20/21/22
R25: Toxic if swallowed.?
R43: May cause sensitization by skin contact.?
R36/37/38: Irritating to eyes, respiratory system and skin.?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 28-36/37-45-36/37/39-26-24-36
S28: After contact with skin, wash immediately with plenty of soap-suds.?
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S24: Avoid contact with skin.?
S36: Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 2
RTECS: UR0785000
HazardClass: 6.1
PackingGroup: III

5.17 Skin, Eye, and Respiratory Irritations
May cause irritation. Remove to fresh air. Flush with copious quantities of water.
5.18 Specification

?Allopurinol , with CAS number of 315-30-0, can be called 4-Hydroxypyrazol[3,4-D]pyrimidine ; 1H-pyrazolo[3,4-d]pyrimidin-4-ol (IM OCS) ; 1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one ; 4-Hydroxypyrazolo(3,4-d)pyrimidine ; 1H-Pyrazolo[3,4-d]pyrimidin-4-ol ; 4-Hydroxypyrazolopyrimidine . Allopurinol (CAS NO.315-30-0) is very slightly soluble in cold water. Insoluble in diethyl ether. It is very slightly soluble in alcohol.

5.19 Toxicity

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

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BLOOD: THROMBOCYTOPENIA
Annals of the Rheumatic Diseases. Vol. 40, Pg. 245, 1981.
man TDLo oral 120mg/kg/4W-I (120mg/kg) BLOOD: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

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) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Medicine. Vol. 76, Pg. 47, 1984

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Skin sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

H317 May cause an allergic skin reaction

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Precursor and Product
9. Computational chemical data
  • Molecular Weight:136.11146g/mol
  • Molecular Formula:C5H4N4O
  • Compound Is Canonicalized:True
  • XLogP3-AA:_0.7
  • Exact Mass:136.03851076
  • Monoisotopic Mass:136.03851076
  • Complexity:190
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:3
  • Topological Polar Surface Area:70.1
  • Heavy Atom Count:10
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
10. Question & Answer
  • Allopurinol is a xanthine oxidase inhibitor that reduces the production of uric acid. Allopurinol is used to prevent gout attacks by reducing uric acid production; high levels of uric acid may cause gout or kidney stones. Allopurinol is available as a generic termed allopurinol. Application Allopur...
  • Allopurinol is xanthine oxidase-activated prodrug of thymidine phosphorylase inhibitor. It is also an important organic intermediate to synthetize substituted pyrimidine products. The following example is about its application on modifications of the thymidine phosphorylase inhibitor. [1] In a reac...
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