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4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol

HCID 1971
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
136470-78-5
Standard SMILES
Nc1nc(NC2CC2)c2ncn(C3C=CC(CO)C3)c2n1
InChIKey
MCGSCOLBFJQGHM-UHFFFAOYSA-N
Molecular formula
C14H18N6O
Average molar mass
286.33 g/mol
Monoisotopic mass
286.15420922

Names & identifiers

Preferred name
4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol
IUPAC
[4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol
English name
Abacavir
Molecular formula
C14H18N6O
Molecular weight
286.33

Names & synonyms

914348-29-1DTXSID208613374-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]-2-cyclopentene-1-methanolRefChem:1069798DTXCID70208894{4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol(4-(2-Amino-6-(cyclopropylamino)-9h-purin-9-yl)cyclopent-2-en-1-yl)methanolC14H18N6ONSC742406[4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanolSCHEMBL464832
Show more names
CS-1071592u89AbacavirAbacavir >Abacavir(base)Abacavir TabletAbacavir, ≥ 98.0%Abacavir USP/EP/BPAbacavir StandardAbacavir - Bio-X ?
SCHEMBL19613805HMS5084H15STL504711AKOS0374879162-Cyclopentene-1-methanol, (1S,4R)-DB-042342CS-0355065EN300-297718

Database identifiers

CAS
136470-78-5、914348-29-1
PubChem CID
1971
DTXSID
DTXSID20861337
Nikkaji
J976.986B

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
102 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
6
Rotatable bonds
4
Heavy atoms
21
Formal charge
0
Complexity
414

Experimental & physicochemical properties

DrugsPharmaceuticals

Physicochemical properties

Melting point
165 ° · 165°
alpha
20 · D20 -59.7°; 43620 -127.8°; 36520 -218.1° (c = 0.15 in methanol)
Boiling point
636 · 636.0±65.0 °C(Predicted)
Density
1.7 · 1.70±0.1 g/cm3(Predicted)
storage temp.
2 · Sealed in dry,2-8°C
solubility
DMSO (Slightly, Heated), Methanol (Slightly)
pka
5.01 · 5.01(at 25℃)
form
Solid
color
Off-White to Pale Beige
Merck
14 · 14,1
BCS Class
3 · 3
CAS DataBase Reference
136470 · 136470-78-5(CAS DataBase Reference)
FDA UNII
2 TIP26VS · WR2TIP26VS
ATC code
5 AF06 · J05AF06
EPA Substance Registry System
2 · 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)- (136470-78-5)
Protein binding
49 % · 49%
Excreted unchanged in urine
2 % · 2%
Volume of distribution
0.8 · 0.8(L/kg)
Biological half-life
1.5 · 1.5 / Unchanged
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
361 · H361-H317-H334-H341
Precautionary statements
501 · P501-P261-P272-P202-P201-P280-P284-P302+P352-P308+P313-P362+P364-P304+P340-P333+P313-P405
RTECS
5979200 · GY5979200
HS Code
2933.99 · 2933.99.7500

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

rtecs
GY5979200
hs_code
2933.99.7500
Signal word
Danger
Symbol(GHS)
GHS08
Hazard statements
H361-H317-H334-H341
Precautionary statements
P501-P261-P272-P202-P201-P280-P284-P302+P352-P308+P313-P362+P364-P304+P340-P333+P313-P405

Chemistry & industry

Applications · 4 items

DescriptionThe drug is extensively metabolized via stepwise phosphorylation to 5′-mono-, di-, and triphosphate. Abacavir is well absorbed (>75%) and penetrates the CNS. The drug can be taken without regard to meals. The drug does not show any clinically significant drug–drug interactions. Abacavir has been reported to produce life-threatening hypersensitivity reactions. The major use of abacavir appears to be in combination with other nucleoside RT inhibitors. A fixed-combination product has recently been approved by the U.S. FDA consisting of 300 mg of ABC, 150 mg of 3TC, and 300 mg of ZDV (Trizivar). The combination has been shown to be superior to other combinations in reducing viral load as well as to show improvement in CD4 cell count.

UsesA nucleoside reverse transcriptase inhibitor (NRTI).

UsesAbacavir is a commonly used nucleoside analogue with potent antiviral activity against HIV-1. - See more at: http://www.selleckchem.com/products/abacavir-sulfate.html#sthash.lApvcTNO.dpuf

General DescriptionAbacavir is a nucleoside reverse transcriptase inhibitorNRTI that has been approved for use in combination therapiesfor the treatment of HIV and AIDS. Once in the tissues,it is metabolized by stepwise phosphorylation to themonophosphate, diphosphate, and triphosphate. Abacavir ishighly bioavailable (>75%) and is effective by the oralroute. It penetrates the blood-brain barrier efficiently.Abacavir has been reported to produce life-threatening hypersensitivityreactions in some patients.

Upstream & downstream products

Upstream raw materials

DibenzoateDibenzoyltartaric acid(1S-cis)-4-Amino-2-cyclopentene-1-methanol(Chloromethylene)dimethyliminium chloride2,5-Diamino-4,6-dihydroxy-pyrimidine2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride2-Amino-4,6-dihydroxypyrimidineCyclopropylamineTriethylamineL(+)-Tartaric acid

Suppliers100 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]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Hong Kong Tiansheng New Material Trading Co., Ltd+8617320695765 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
上海贝美医药科技有限公司21-33738120 15000110506 · [email protected]
上海特伯化学科技有限公司+86-21-60341587 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海遐瑞医药科技有限公司+86 21 61551611
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
Shanghai Witofly Chemical Co.,Ltd[email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
杭州六可生物科技有限公司+86-571-86912261 19975279805 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
西安天广源生物科技有限公司+86-029-86333380 +86-18829239519 · [email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
Qiuxian Baitai New Material Co., LTD+86-19932103556 · [email protected]
BOC Sciences16314854226 · [email protected]
药渡经纬信息科技(北京)有限公司+86-400-851-9921 · [email protected]
广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
南京博米尔生物科技有限公司025-83453382-8005 · [email protected]
Target molecule Corp.857-239-0968 · [email protected]
成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Abacavir is a 2,6-diaminopurine that is (1S)-cyclopent-2-en-1-ylmethanol in which the pro-R hydrogen at the 4-position is substituted by a 2-amino-6-(cyclopropylamino)-9H-purin-9-yl group. A nucleoside analogue reverse transcriptase inhibitor (NRTI) with antiretroviral activity against HIV, it is used (particularly as the sulfate) with other antiretrovirals in combination therapy of HIV infection. It has a role as a HIV-1 reverse transcriptase inhibitor, an antiviral drug and a drug allergen.

Related reactions

2 records
New reaction record
HRID 100586 reaction equation
HRID 100586As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 208412 reaction equation
HRID 208412As productTraining data from https://doi.org/10.1039/C8SC04228D (6/10)

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes