基本情報
- 標準SMILES
COc1cc(NC(C)CCCN)c2ncccc2c1.O=P(O)(O)O.O=P(O)(O)O- InChIKey
GJOHLWZHWQUKAU-UHFFFAOYSA-N- 分子式
- C15H27N3O9P2
- 平均分子量
- 455.34 g/mol
- 単同位体質量
- 455.12225344
名称と識別子
- 優先名称
- Primaquine Diphosphate
- IUPAC
- 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid
- 現地名
- プリマキンリン酸塩
- 英語名
- Primaquine diphosphate
- 分子式
- C15H27N3O9P2
- 分子量
- 455.34
名称と別名
名称をさらに表示
データベース識別子
- CAS
63-45-6- PubChem CID
- 6135
- DTXSID
DTXSID6045248- ChEMBL
CHEMBL43128- ChEBI
CHEBI:232993- UNII
- H0982HF78B
- EC Number
- 200-560-8
物性
構造計算による物性
- 極性表面積
- 216 Ų
- 水素結合供与体数
- 8
- 水素結合受容体数
- 12
- 回転可能結合数
- 6
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 312
実験および物理化学的性質
物理化学的性質
- 融点
- 205 · 205-206 °C (dec.)(lit.)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 50 mg/mL、透明、オレンジ色から赤色 · 水: 可溶50mg/mL、透明、オレンジ色から赤色
- 外見
- Solid
- 色
- Red brown to orange
- 水溶解度
- 適度に溶ける
- Merck
- 13 · 13,7833
- BRN
- 3812133 · 3812133
- BCS Class
- 1 · 1 (CLogP), 3 (LogP)
- 安定性
- 安定。強力な酸化剤とは相容れない。
- 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
- CAS データベース
- 63 · 63-45-6(CAS DataBase Reference)
化学的性質
化学的特性orange powder
安全と法規制
GHS分類
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.
危険有害性情報
毒性情報
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.
安全データ
- F
- 10
- wgk
- 3
- rtecs
- VA9660000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29334900
- risk_code
- 25
- hazard_code
- T
- safety_code
- 45
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 OralMuta. 2Repr. 2
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
FDA Pharmacological Classification
PRIMAQUINE PHOSPHATE
Antimalarial [EPC]
応用分野
使用Primaquine 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.
調製方法
純化方法It forms yellow crystals from 90% aqueous EtOH and is moderately soluble in H2O. The oxalate salt has m 182.5-185o (from 80% aqueous EtOH), and the free base is a viscous liquid b 165-170o/0.002mm, 175-177o/2mm. [Elderfield et al. J Am Chem Soc 68 1526 1964, Elderfield et al. J Am Chem Soc 77 4817 1955, Beilstein 22 III/IV 5817.]
上流・下流製品情報
上流原料
サプライヤー50 社
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