Basic information
- CAS
99464-64-9- Standard SMILES
CCOC(=O)OC(C)OC1=C(C(=O)Nc2ccccn2)N(C)S(=O)(=O)c2ccccc21- InChIKey
LSNWBKACGXCGAJ-UHFFFAOYSA-N- Molecular formula
- C20H21N3O7S
- Average molar mass
- 447.5 g/mol
- Monoisotopic mass
- 447.11002119
Overview
Ampiroxicam is a benzothiazine that is the 1-[(ethoxycarbonyl)oxy]ethyl ether of piroxicam. A prodrug for piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis. It has a role as a non-steroidal anti-inflammatory drug, an analgesic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antirheumatic drug and a prodrug. It is a monocarboxylic acid amide, a sulfonamide, an aminopyridine, a benzothiazine, an etabonate ester and an acetal. It is functionally related to a piroxicam.
Names & identifiers
- Preferred name
- Ampiroxicam
- IUPAC
- ethyl 1-[[2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1λ6,2-benzothiazin-4-yl]oxy]ethyl carbonate
- English name
- Ampiroxicam
- Molecular formula
- C20H21N3O7S
- Molecular weight
- 447.46
Names & synonyms
ampiroxicam99464-64-9FlucamAmpiroxicamumCP 65703CP-65703DTXSID60464740PV32JZB1JNSC-759807CHEBI:31210CP-65,703DTXCID4026474
Show more names
NasilAmpiroamAmpiroxicam 98%Ampiroxicam(CP 65703)Ampiroxicam USP/EP/BPAmpiroxicam - Bio-X ?99464-64-9 Ampiroxicam
(+-)-4-(1-Hydroxyethoxy)-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide ethyl carbonate (ester), 1,1-dioxideRefChem:557922807-877-6Ethyl (1RS)-1-((2-methyl-1,1-dioxido-3-((pyridin-2-ylamino)carbonyl)-2H-1,2-benzothiazin-4-yl)oxy)ethyl carbonateAmpiroxicam [INN:BAN:JAN]AMPIROXICAM [MI]AMPIROXICAM [WHO-DD]ethyl (1-((2-methyl-1,1-dioxido-3-(pyridin-2-ylcarbamoyl)-2H-benzo[e][1,2]thiazin-4-yl)oxy)ethyl) carbonate
Database identifiers
- CAS
99464-64-9- PubChem CID
- 2176
- DTXSID
DTXSID6046474- ChEMBL
CHEMBL1566249- ChEBI
CHEBI:31210
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 133 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 8
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 808
Physicochemical properties
- Melting point
- 159 · 159-161C
- Density
- 1.44 · 1.44±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 12.74 · 12.74±0.20(Predicted)
- color
- White to Off-White
- CAS DataBase Reference
- 99464 · 99464-64-9(CAS DataBase Reference)
- FDA UNII
- 0 PV32JZB1J · 0PV32JZB1J
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- Toxicity
- 50 orally · LD50 orally in male, female rats: 1798, 747 mg/kg (Iijima)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Ampiroxicam
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- Toxicity
- LD50 orally in male, female rats: 1798, 747 mg/kg (Iijima)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
DescriptionAmpiroxicam is a once-daily non-steroidal anti-inflammatory drug (NSAID) introduced in Japan. As a non-acidic ether carbonate prodrug of the widely used antiinflammatory agent, piroxicam, ampiroxicam is similar or more potent than piroxicam in suppressing carrageenan edema, ultraviolet erythema, traumatic edema, capillary permeability, acetic acid writhing, yeast algesia and yeast hyperthermia in many animals. Eioavailability studies in man show undetectable plasma levels of ampiroxicam indicating 100% conversion to piroxicam during absorption process. Ampiroxicam has been reported to have fewer side effects on the gastric mucosa than piroxicam.
UsesProdrug of Piroxicam. Anti-inflammatory.
Usesantiinflammatory, analgesic
Upstream & downstream products
Upstream raw materials
Suppliers86 total
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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