캅토프릴
캅토프릴 · on · acidic · captoril · (2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid · capoten · (2S)-1-[(2S)-3-Mercapto-2-methylpropionyl]-2-pyrrolidinecarboxylic acid · Timolo

식별자 및 물리적 특성
| CAS No. | 62571-86-2 |
|---|---|
| 분자식 | C9H15NO3S |
| 평균 분자량 | 217.29 g/mol |
| 단동위원소 질량 | 217.07726434 g/mol |
| SMILES | C[C@H](CS)C(=O)N1CCC[C@H]1C(=O)O |
| InChIKey | FAKRSMQSSFJEIM-RQJHMYQMSA-N |
| PubChem CID | 44093 |
| ChEMBL | CHEMBL1560 |
| ChEBI | CHEBI:3380 |
| EC No. | 263-607-1 |
| DTXSID | DTXSID1037197 |
| 현지명 | 캅토프릴 |
화학 및 물리적 성질
| XLogP | 0.3 |
|---|---|
| 극성 표면적 | 58.6 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 14 |
| 형식 전하 | 0 |
| 복잡도 | 244 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antihypertensives |
| LogP(분배 계수) | log Kow = 0.340.6 |
| 냄새 | Slight sulfurous odor |
| Color/Form | White to off-white, crystalline powderCrystals from ethyl acetate/hexane |
| 용해도 | Freely solubleFreely soluble in water (approximately 160 mg/mL)Freely soluble in alcohol, chloroform, methylene chloridesparingly soluble in ethyl acetate4.52e+00 g/LH2O: 0.1 g/mL, 매우 약간 흐릿함, 무색 |
| Human Drugs | Breast FeedingLactationMilk, HumanAntihypertensive AgentsAngiotensin-Converting Enzyme InhibitorsACE InhibitorsFDA approved drugs -> Active ingredientPharmaceuticals |
| Decomposition | When heated to decomposition it emits every toxic fumes of /nitrogen oxides and sulfur oxides/ |
| 녹는점 | 103-104103-104 °C106 °C104-108 °C (lit.) |
| Optical Rotation | Specific optical rotation: -131.0 deg at 22 °C/D (c = 1.7 in ethanol) |
| Physical Description | Solid |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Dissociation Constants | pKa1 = 3.7pKa2 = 9.8 |
| 끓는 점 | 427.0±40.0 °C(Predicted) |
| 밀도 | 1.2447 (rough estimate) |
| 굴절률 | -127.5 ° (C=1.7, EtOH) |
| 저장 조건 | room temp |
| 물리적 상태 | 결정성 분말 |
| pKa(산도 계수) | 3.7, 9.8(at 25℃) |
| 색상 | 흰색에서 황백색까지 |
| 생물학적 소스 | synthetic (organic) |
| 용해도 | 녹는 |
| Merck | 14,1774 |
| BRN | 477887 |
| BCS Class | 3 |
| 안정성 | 안정적인. 강한 산화제와 호환되지 않습니다. |
| InChI | 1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1 |
| InChIKey | FAKRSMQSSFJEIM-RQJHMYQMSA-N |
| SMILES | C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O |
| NIST | Captopril(62571-86-2) |
화학적 성질
White or almost white, crystalline powder.
안전 및 규제
| GHS 분류 | DangerH317 (95.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]P203, P261, P264+P265, P272, P280, P302+P352, P305+P354+P338, P317, P318, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 137 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H317: May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| 규제 정보 | Captopril: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | IMAP assessments - L-Proline, 1-(3-mercapto-2-methyl-1-oxopropyl)-, (S)-: Environment tier I assessment |
| FDA 요건 | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including captopril, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| Special Reports | Raia JJ Jr et alAngiotensin-converting Enzyme Inhibitors: A Comparative ReviewDICP 24 (5): 506-25 (1990) The chemistry, pharmacology, pharmacokinetics, adverse effects, and dosages of the three currently available angiotensin converting enzyme (ACE) inhibitors are reviewed.Brogden RN et alDrugs 36 (Nov): 540-600 (1988)A review of the pharmacodynamics, pharmacokinetics, therapeutic trials, side effects, overdosage, interactions and dosage and administration of captopril is presented. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), sulfur oxides. |
| Hazard Classes and Categories | Skin Sens. 1 (95.6%) |
| 소화 절차 | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. |
| 보관 조건 | Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place. |
용도
개요
Captopril is the most studied of the angiotensin-converting enzyme inhibitors proposed as an antihypertensive drug. It blocks angiotensin-converting enzyme, which suppresses formation of angiotensin II and relieves its vasoconstricting effect on arterial and venous vessels. Overall vascular peripheral tension is reduced, which results in the lowering of arterial pressure.
용도
Captopril has also been shown to inhibit the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density. Captopril demonstrates noncompetitive inhibition of tyrosinase monophenolase activity and competitive inhibition of diphenolase activity
일반 설명
Captopril, 1-[(2S)-3-mercapto-2-methyl-1-oxopropionyl]proline (Capoten), blocks the conversion of angiotensinI to angiotensin II by inhibiting the convertingenzyme. The rational development of captopril as an inhibitorof ACE was based on the hypothesis that ACE and carboxypeptidaseA functioned by similar mechanisms. It wasnoted that d-2-benzylsuccinic acid was a potent inhibitor ofcarboxypeptidase A, but not ACE. By use of this small molecule as a prototype, captopril was designed with a carboxylgroup on a proline and a thiol group was introduced toenhance the binding to the zinc ion of ACE. The importantbinding points at the active site of ACE are thought to be anarginine residue, which provides a cationic site that attracts acarboxylate ion, and a zinc ion, which can polarize a carbonylgroup of an amide function to make it more susceptible to hydrolysis.Hydrophobic pockets lie between these groups in theactive site, as does a functional group that forms a hydrogenbond with an amide carbonyl.