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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27N5
Molecular Weight 349.4726
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MAVORIXAFOR

SMILES

NCCCCN(CC1=NC2=C(N1)C=CC=C2)[C@H]3CCCC4=CC=CN=C34

InChI

InChIKey=WVLHHLRVNDMIAR-IBGZPJMESA-N
InChI=1S/C21H27N5/c22-12-3-4-14-26(15-20-24-17-9-1-2-10-18(17)25-20)19-11-5-7-16-8-6-13-23-21(16)19/h1-2,6,8-10,13,19H,3-5,7,11-12,14-15,22H2,(H,24,25)/t19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H27N5
Molecular Weight 349.4726
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.evaluategroup.com/Universal/View.aspx? type=Story&id=99438 http://adisinsight.springer.com/drugs/800017499

AMD-070 is a small molecule drug candidate that belongs to a new investigational class of anti-HIV drugs known as entry (fusion) inhibitors. Approximately 76% of HIV-patients with measurable viral load are infected with a strain of virus that is resistant to one or more classes of antiretroviral agents, thus reducing treatment options. Unlike many existing HIV drugs that target the virus after it has infected a healthy cell, AMD-070 blocks the virus from entering a healthy cell, thus preventing the replication process. AMD-070 targets the CXCR4 receptor on HIV and prevents the virus from entering and infecting healthy cells. AMD-070 is specific for the CXCR4 receptor and does not interact with any other chemokine receptors in vitro. AMD-070 strongly inhibits viral infection by all CXCR4 using virus (including virus using CXCR4 alone and/or virus using CXCR4 and CCR5) in vitro. AMD-070 is orally bioavailable in animals, it has suitable PK and toxicity profile for oral dosing. AMD-070 shows additive or synergistic effects in vitro in combination with other known anti-HIV agents. AMD-070 is active against CXCR4 using HIV strains that are resistant to existing antiretroviral therapies in vitro, reveals potent anti-HIV activity against CXCR4-using laboratory strains and clinical isolates. MD-070 had been in phase II clinical trials by Genzyme for the treatment of HIV infection. However, this research has been discontinued. AMD-070 has been studied in Phase I/II clinical trials for the treatment of Renal cell carcinoma and Phase I clinical trials for the treatment of malignant melanoma and solid tumours.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 nM [IC50]
13.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
514 ng/mL
100 mg 1 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
633 ng/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
117 ng/mL
20 mg 2 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
956 ng/mL
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2260 ng/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2430 ng/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1089.99 ng × h/mL
100 mg 1 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1680 ng × h/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
262 ng × h/mL
20 mg 2 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3830 ng × h/mL
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8060 ng × h/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
9500 ng × h/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMD-070 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
400 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
healthy
n = 6
Health Status: healthy
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery of novel small molecule orally bioavailable C-X-C chemokine receptor 4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication.
2010 Apr 22
Patents

Sample Use Guides

200 mg of AMD-070 was given twice daily over 10 days.
Route of Administration: Oral
AMD-070 inhibited the replication of T-tropic HIV-1 (NL4.3 strain) in MT-4 cells and PBMCs with an IC(50) of 2 and 26 nM, respectively, while remaining noncytotoxic to cells at concentrations exceeding 23 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:22 UTC 2023
Edited
by admin
on Fri Dec 15 15:41:22 UTC 2023
Record UNII
0G9LGB5O2W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MAVORIXAFOR
INN   USAN  
Official Name English
N1-(1H-BENZIMIDAZOL-2-YLMETHYL)-N1-((S)-5,6,7,8-TETRAHYDROQUINOLIN-8-YL)-BUTANE-1,4-DIAMINE
Systematic Name English
X4P001
Brand Name English
mavorixafor [INN]
Common Name English
1,4-BUTANEDIAMINE, N1-(1H-BENZIMIDAZOL-2-YLMETHYL)-N1-((8S)-5,6,7,8-TETRAHYDRO-8-QUINOLINYL)-
Systematic Name English
MAVORIXAFOR [USAN]
Common Name English
AMD11070
Code English
X 4P-001
Code English
Mavorixafor [WHO-DD]
Common Name English
AMD-11070
Code English
CXCR4 INHIBITOR X4P-001
Common Name English
1,4-BUTANEDIAMINE, N-(1H-BENZIMIDAZOL-2-YLMETHYL)-N-((8S)-5,6,7,8-TETRAHYDRO-8-QUINOLINYL)-
Systematic Name English
AMD070
Code English
AMD-070
Code English
X4P-001
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 887322
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
FDA ORPHAN DRUG 500115
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
Code System Code Type Description
INN
10724
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID60971247
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
CAS
558447-26-0
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
NCI_THESAURUS
C126660
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
FDA UNII
0G9LGB5O2W
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
CAS
690656-53-2
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
SUPERSEDED
SMS_ID
100000178380
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
PUBCHEM
11256587
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
USAN
GH-17
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
DRUG BANK
DB05501
Created by admin on Fri Dec 15 15:41:22 UTC 2023 , Edited by admin on Fri Dec 15 15:41:22 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
Related Record Type Details
ACTIVE MOIETY