기본 정보
- 표준 SMILES
COc1cc(NC(C)CCCN)c2ncccc2c1.O=P(O)(O)O.O=P(O)(O)O- InChIKey
GJOHLWZHWQUKAU-UHFFFAOYSA-N- 분자식
- C15H27N3O9P2
- 평균 분자량
- 455.34 g/mol
- 단동위원소 질량
- 455.12225344
이름 및 식별자
- 우선 이름
- Primaquine Diphosphate
- IUPAC
- 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid
- 현지명
- 프리마퀸 비스포스페이트
- 영어명
- Primaquine diphosphate
- 분자식
- C15H27N3O9P2
- 분자량
- 455.34
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
63-45-6- PubChem CID
- 6135
- DTXSID
DTXSID6045248- ChEMBL
CHEMBL43128- ChEBI
CHEBI:232993- UNII
- H0982HF78B
- EC Number
- 200-560-8
물성
구조 계산 물성
- 극성 표면적
- 216 Ų
- 수소 결합 공여자 수
- 8
- 수소 결합 수용자 수
- 12
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 29
- 형식 전하
- 0
- 복잡도
- 312
실험 및 물리화학적 성질
물리화학적 성질
- 녹는점
- 205 · 205-206 °C (dec.)(lit.)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 50 mg/mL, · 물: 용해성50mg/mL, 투명, 주황색~빨간색
- 물리적 상태
- Solid
- 색상
- Red brown to orange
- 수용성
- 적당히 용해됨
- Merck
- 13 · 13,7833
- BRN
- 3812133 · 3812133
- BCS Class
- 1 · 1 (CLogP), 3 (LogP)
- 안정성
- 안정적인. 강한 산화제와 호환되지 않습니다.
- InChI
- InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)
- InChIKey
- GJOHLWZHWQUKAU-UHFFFAOYSA-N
- SMILES
- C1(NC(C)CCCN)=CC(=CC2=CC=CN=C12)OC.P(=O)(O)(O)O.P(=O)(O)(O)O
화학적 성질
orange powder
안전 및 규제
GHS 분류
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
독성 정보
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Primaquine phosphate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Primaquine and its metabolite are poorly excreted into breastmilk of nursing mothers and undetectable in the serum of their breastfed infants. Breastfed infants beyond the neonatal period have shown no evidence of hemolysis. Neonates and infants with glucose-6-phosphate dehydrogenase (G6PD) deficiency have not been studied, but G6PD-deficient infants over 28 days of age appear to have a low risk of hemolysis from exposure in breastmilk. Modeling suggests that nursing mothers can receive primaquine with little risk to their infants, even if the infants are G6PD deficient.;United Kingdom malaria treatment guidelines recommend that primaquine be avoided in nursing mothers with malaria and that weekly chloroquine 500 mg be given until breastfeeding is completed. However, these guidelines were developed before information on the excretion of primaquine into breastmilk and safety in breastfed infants was published. More recent information indicates that all mothers nursing infant over 28 days of age could safely receive primaquine. The Centers for Disease Control and Prevention guidelines state that primaquine may be used in breastfeeding mothers and infants with normal G6PD levels. Because the small amounts of primaquine transferred in breast milk are insufficient to provide adequate protection or treatment of malaria, infants who require chemoprophylaxis or therapy must receive the recommended dosages of primaquine.;◉ Effects in Breastfed Infants;Twenty-one mothers with vivax malaria were given a dosage of primaquine 0.5 mg/kg daily for 14 days while breastfeeding their infants who were at least 28 days old. No alterations in hematocrit, Heinz body counts, serum bilirubin, oxygen saturation, or methemoglobinemia were seen in any of the infants.;A woman with vivax malaria who was 5 months postpartum was given a dose of primaquine of 0.52 mg/kg daily for 7 days, then 0.46 mg/kg daily for 7 days after rechecking the patient’s weight. She was found to be heterozygous for glucose-6-phosphate dehydrogenase (G6PD) deficiency and experienced some hemolysis and anemia. Her female infant was being breastfed (extent not stated) during treatment and was found to be heterozygous for the G6PD Mahidol variant, but had no apparent hemolysis. The child’s vaccination schedule was completed, and the 6-month motor milestones were normal.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
안전 데이터
- wgk
- 3
- rtecs
- VA9660000
- ridadr
- UN 2811 6.1/PG 3
- HS 번호
- 29334900
- risk_code
- 25
- hazard_code
- T
- safety_code
- 45
- 포장분류
- III
- 위험 등급
- 6.1(b)
- F 고인화성물질
- 10
- Hazard Classifications
- Acute Tox. 3 OralMuta. 2Repr. 2
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
화학 및 산업
약리 정보
FDA Pharmacological Classification
PRIMAQUINE PHOSPHATE
Antimalarial [EPC]
응용 분야
용도Primaquine diphosphate is an established antimalarial drug used in the treatment of persistent liver forms of P. vivax or P. ovale infection for its ability to kill late-stage gametocytes and hypnozoites. In historical terms, this aminoquinoline was the stimulus for the discovery of glucose-6-phosphate (G6P) dehydrogenase deficiency as it induced hemolytic anemia in patients lacking the G6P-metabolizing enzyme.
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