Camptothecin
CAMPTOTHECIN · CAMPTOTHECINE · CaMpathecin · (S)-(+)-CAMPTOTHECIN · (20S)-CAMPTOTHECIN · 5,6-DIHYDROXY-7-GLUCURONOSYLFLAVONE · CAMPTOTHECIN, CAMPTOTHECA ACUMINATA · 1,6-DIHYDROXY-7-GLUCURONOSYLFLAVONE
식별자 및 물리적 특성
| CAS No. | 7689-03-4 |
|---|---|
| 분자식 | C20H16N2O4 |
| 평균 분자량 | 348.4 g/mol |
| 단동위원소 질량 | 348.11100699 g/mol |
| SMILES | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccccc3nc2-1 |
| InChIKey | VSJKWCGYPAHWDS-FQEVSTJZSA-N |
| PubChem CID | 24360 |
| ChEMBL | CHEMBL65 |
| ChEBI | CHEBI:27656 |
| EC No. | 444-280-6 |
| DTXSID | DTXSID0030956 |
화학 및 물리적 성질
| XLogP | 1 |
|---|---|
| 극성 표면적 | 79.7 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 26 |
| 형식 전하 | 0 |
| 복잡도 | 742 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics |
| 녹는점 | 275-277 °C260 °C (dec.)(lit.) |
| Collision Cross Section | 178.35 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]181.9 Ų [M+H]+ [CCS Type: TW |
| 끓는 점 | 482.73°C (rough estimate) |
| 밀도 | 1.3112 (rough estimate) |
| 굴절률 | 1.5700 (estimate) |
| 저장 조건 | 2-8°C |
| 용해도 | 클로로포름/메탄올(4:1): 4mg/mL |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | pKa 10.83 (Uncertain) |
| 색상 | 노란색 |
| 용해도 | 불용성 |
| Merck | 14,1735 |
| BRN | 631069 |
| 안정성 | 제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다. |
| InChI | 1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1 |
| InChIKey | VSJKWCGYPAHWDS-FQEVSTJZSA-N |
| SMILES | CC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5ccccc5nc34)C2=O |
| LogP(분배 계수) | 1.740 |
화학적 성질
light yellow crystal powde
안전 및 규제
| GHS 분류 | DangerH301 (98%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301 (97.1%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| 규제 정보 | Status: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/4979 |
| Hazard Classes and Categories | Acute Tox. 3 (98%)Acute Tox. 3 (97.1%) |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | UQ0492000 |
| 운송 번호(UN) | UN 1544 6.1/PG 3 |
| 관세 코드 | 29399990 |
| 위험 문구(R) | 36/37/38-25-20/21/22 |
| 위험 표시 | T,Xi,Xn |
| 안전 문구(S) | 45-36/37/39-26-36 |
| 포장분류 | Ⅲ |
| 위험 등급 | 6.1Acute Tox. 3 OralMuta. 1B |
| 위험 참고 사항 | Irritant |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
용도
개요
Camptothecin is an alkaloid derived from Xi Shu (Camptotheca acuminata), which belongs to Nyssaceae. The traditional Chinese medicine Camptotheca acuminata (Xi Shu) has been collected in the Compilation of Chinese Herbal Medicine, Chinese Materia Medica, and Great Dictionary of Chinese Medicine. Camptotheca acuminata (Xi Shu) is widely distributed in the basin of Yangtze river and the southwestern provinces. The main medicinal parts of Camptotheca acuminata (Xi Shu) are root bark and fruit, which get rid of heat and toxic materials and eliminate the disease.
역사
In 1966, Wall M E et al. from the United States isolated an alkaloid from Camptotheca acuminata and defined its chemical structure. The invitro anticancer tests revealed the anticancer activity of the tryptophan-terpene alkaloid, which is known as camptothecin and received widely concern. In 1975, Corey etal. first opened the door for the chiral synthesis of camptothecin, but the reaction step was long and the yield rate was very low. It was not until 1997 that Ciufolini etal. developed a new method for the synthesis of camptothecin by five steps, with a total yield rate up to 51%. The great breakthrough in the chemical synthesis of camptothecin has made its extensive application become a reality.Hydroxycamptothecin, as a camptothecin derivative with a hydroxyl group on the tenth carbon atom, is widely used for the treatment of various cancers. In 1969, researchers from Shanghai Institute of Materia Medica found that hydroxycamptothecin possessed potent anticancer activity and low toxicity. And this finding promoted the production and clinical application of hydroxycamptothecin, but its usage was interrupted for technology and quality. In the 1980s, hydroxycamptothecin was reproduced for clinical application with an improvement in producing technology, and hydroxycamptothecin got its approval number in 1986 for clinical usage in China. In the 1990s, the US Food and Drug Administration approved the clinical application of topotecan and irinotecan, which played a significant role in the prevention and treatment of cancers.
용도
Antitumor alkaloid. Binds irreversible to the DNA-topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and traps the enzyme in a covalent linkage with DNA. A cytotoxic antitumor agent