ChemicalBook > CAS DataBase List > Abacavir

Abacavir

Product Name
Abacavir
CAS No.
136470-78-5
Chemical Name
Abacavir
Synonyms
CS-107;1592u89;Abacavir;Abacavir >Abacavir(base);Abacavir Tablet;Abacavir, ≥ 98.0%;Abacavir USP/EP/BP;Abacavir Standard;Abacavir (see A105000)
CBNumber
CB5698138
Molecular Formula
C14H18N6O
Formula Weight
286.33
MOL File
136470-78-5.mol
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Abacavir Property

Melting point:
165°
alpha 
D20 -59.7°; 43620 -127.8°; 36520 -218.1° (c = 0.15 in methanol)
Boiling point:
636.0±65.0 °C(Predicted)
Density 
1.70±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
DMSO (Slightly, Heated), Methanol (Slightly)
pka
5.01(at 25℃)
form 
Solid
color 
Off-White to Pale Beige
Merck 
14,1
BCS Class
3
CAS DataBase Reference
136470-78-5(CAS DataBase Reference)
EPA Substance Registry System
2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)- (136470-78-5)
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Safety

RTECS 
GY5979200
HS Code 
2933.99.7500
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H341Suspected of causing genetic defects

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical
Product number
A2694
Product name
Abacavir
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$128
Updated
2024/03/01
TCI Chemical
Product number
A2694
Product name
Abacavir
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$435
Updated
2024/03/01
Usbiological
Product number
001006
Product name
Abacavir
Packaging
5mg
Price
$312
Updated
2021/12/16
Usbiological
Product number
295285
Product name
Abacavir
Packaging
1g
Price
$340
Updated
2021/12/16
TRC
Product number
A104990
Product name
Abacavir
Packaging
500mg
Price
$185
Updated
2021/12/16
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Abacavir Chemical Properties,Usage,Production

Description

The 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.

Originator

Ziagen ,GlaxoSmithKline

Uses

A nucleoside reverse transcriptase inhibitor (NRTI).

Uses

Abacavir 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

Indications

Abacavir (Ziagen) is a guanosine nucleoside analogue indicated for the therapy of HIV-1 infection in adults and children. It is used as part of a multidrug regimen and is available in a fixed-dose combination with zidovudine and lamivudine (Trizivir). It is also used for postexposure HIV infection prophylaxis.

Definition

ChEBI: 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.

Manufacturing Process

Treatment of 2,5-diamino-4,6-dihydroxypyrimidine (I) with (chloromethylene)dimethylammonium chloride yielded the dichloropyrimidine with both amino groups derivatized as amidines. Partial hydrolysis with aqueous HCl in hot ethanol gave N-(2-amino-4,6-dichloro-pyrimidin-5-yl)-N,Ndimethylformamidene (II). Subseqent buffered hydrolysis at pH 3.2 yielded the (2-amino-4,6-dichloro-pyrimididin-5-ylamino)acetaldehyde (III). Condensation chloropyrimidine (III) with (1S,4R)-4-amino-2-cyclopentene-1- methanol (IV) in the presence of triethylamine and NaOH gave [2-amino-4- chloro-6-(4-hydroxymethyl-cyclopent-2-enylamino)pyrimidin-5-ylamino]- acetaldehyde (V). The correct enantiomer (IV) of racemic aminocyclopentene was obtained by resolution of diastereomeric salts with D-dibenzoyltartaric acid. Cyclization of (V) to the corresponding purine was accomplished with refluxing triethyl orthoformate or diethoxymethyl acetate to give nucleoside analogue [4-(2-amino-6-chloro-purin-9-yl)-cyclopent-2-enyl]methanol (VI). Displacement of chloride in the purine nucleus with cyclopropyl amine in refluxing butanol afforded abacavir. The structure of obtained compound was confirmed by 1H NMR method and elemental analysis.
In practice it is usually used as sulfate salt.

Therapeutic Function

Antiviral

Antimicrobial activity

Abacavir has activity against HIV-1, HIV-2 and human T-cell lymphotrophic virus type-1 (HTLV-1).

Acquired resistance

Resistance is associated with specific changes in codons 184 with 65, 74 or 115 in the HIV reverse transcriptase codon region.

General Description

Abacavir 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.

Pharmaceutical Applications

A synthetic analog of guanine formulated for oral use.

Pharmacokinetics

Oral absorption: 83%
Cmax 300 mg oral, twice daily: 3.0 ± 0.89 mg/L
600 mg once daily: 4.26 mg/L
Plasma half-life: 1.5 h
Volume of distribution: 0.8 L/kg
Plasma protein binding: c. 49%
Absorption
After oral administration abacavir sulfate undergoes rapid and extensive absorption unaffected by food.
Distribution
It penetrates well into the cerebrospinal fluid (CSF) and is an NRTI of choice if this characteristic is thought desirable. Good penetration into the male genital tract has been observed. The drug is secreted into human breast milk.
Metabolism
It is primarily metabolized in the liver, mainly by alcohol dehydrogenase and glucuronidation.
Excretion
Around 83% of the dose is eliminated in the urine, <2% as unchanged drug; the remainder is excreted in the feces. Dose adjustment is unnecessary in renal impairment. It can be used in moderate hepatic impairment, but is contraindicated if dysfunction is severe.

Clinical Use

Treatment of HIV infection in adults and children (in combination with other antiretroviral drugs)

Side effects

Abacavir is associated with side effects such as anorexia, nausea, vomiting, malaise, headache, and insomnia. A potentially fatal hypersensitivity reaction develops in approximately 5% of patients, usually early in the course of treatment. Fever and rash are the most common symptoms of this reaction; malaise, respiratory symptoms, and gastrointestinal complaints may also occur. Resistance to abacavir may be associated with resistance to zidovudine, didanosine, and lamivudine.

Side effects

Life-threatening hypersensitivity reactions occur in 5–8% of all individuals, necessitating discontinuation of the drug. Typically patients present within the first 6 weeks of starting treatment with fever, rash or other symptoms that worsen in severity with continued drug exposure. Hypersensitivity is associated with carriage of the major histocompatibility complex class I allele HLA-B57*01 and screening for this allele can significantly reduce the incidence of this effect.
Current or recent (within the preceding 6 months) use of abacavir has been associated with a risk of myocardial infarction, but studies have yielded conflicting data.

Drug interactions

Potentially hazardous interactions with other drugs
Antivirals: possibly reduces effects of ribavirin; concentration reduced by tipranavir.
Orlistat: absorption possibly reduced by orlistat.

Metabolism

Abacavir is primarily metabolised by the liver with approximately 2% of the administered dose being renally excreted, as unchanged compound. The primary pathways of metabolism in man are by alcohol dehydrogenase and by glucuronidation to produce the 5'-carboxylic acid and 5'-glucuronide which account for about 66% of the administered dose. The metabolites are excreted in the urine.

Abacavir Preparation Products And Raw materials

Raw materials

Preparation Products

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Abacavir Suppliers

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View Lastest Price from Abacavir manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Abacavir 136470-78-5
Price
US $0.00/G
Min. Order
50G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-02
Henan Fengda Chemical Co., Ltd
Product
Abacavir 136470-78-5
Price
US $5.00-0.10/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-16
Hong Kong Tiansheng New Material Trading Co., Ltd
Product
Abacavir 136470-78-5
Price
US $6.10/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000tons
Release date
2021-12-23

136470-78-5, AbacavirRelated Search:

EC 2.6.1.2 Methyl cyclopentenolone Glycine 4-Amino-benzenesulfonic acid monosodium salt 6-Aminocaproic acid ALTRENOGEST Tris(hydroxymethyl)aminomethane Acetaminophen Glucosamine Sulfamic acid Cyclopentene ABACAVIR SULFATE,ABACAVIR SULPHATE N-(2-AMINO-4,6-DICHLOROPYRIMIDIN-5-YL) FORMAMIDE[FOR ABACAVIR] (1S-cis)-4-Amino-2-cyclopentene-1-methanol Purine Abacavir trans-Abacavir Hydrochloride Abacavir Related CoMpound D

  • 1592u89
  • [(1s,4r)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1-cyclopent-2-enyl]methanol
  • [(1S,4R)-4-(2-AMINO-6-CYCLOPROPYLAMINO-PURIN-9-YL)-CYCLOPENT-2-ENYL]-METHANOL
  • 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)-
  • 2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S-cis)-
  • (+/-)-4-[2-amino-6-(cyclopropylamino)-9h-purin-9-yl]-2-cyclopentene-1-methanol
  • Abacavir
  • Abacavir (see A105000)
  • Abacavir-(1R,trans)-isoMer
  • Abacavir-5'-tert-butyl ether
  • (1S-cis)-4-[2-AMino-6-(cyclopropylaMino)-9H-purin-9-yl]-2-cyclopentene-1-Methanol
  • Abacavir(base)
  • [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9-purinyl]-1-cyclopent-2-enyl]methanol
  • CS-107
  • [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol
  • Abacavir &gt
  • ({(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-Purin-9- yl]cyclopent-2-en-l-yl} methanol)
  • Abacavir USP/EP/BP
  • Abacavir (1.0 mg/mL in Methanol)
  • {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9Hpurin-9-yl]cyclopent-2-en-1-yl}methanol
  • abacavir D5Q: What is abacavir D5 Q: What is the CAS Number of abacavir D5
  • Abacavir Tablet
  • Abacavir Standard
  • Abacavir Manufacturer/High quality/Best price/In stock CAS NO.136470-78-5
  • ((1S,4R)-4-(2-Amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol[Abacavir
  • Abacavir, ≥ 98.0%
  • Abacavir-d4 5’-4-Chloro-6-methylpyrimidine-2,5-diamine
  • Abacavir, 10 mM in DMSO
  • 136470-78-5
  • C14H18N6O
  • Heterocycles
  • Bases & Related Reagents
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Nucleotides
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