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Compound Detail

CHEMBL525076

ENFUVIRTIDE
💊 Approved Drug
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💊 Approved Drug
CC[C@H](C)[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Basic Information

ChEMBL ID CHEMBL525076
Name ENFUVIRTIDE
Phase Approved
Structure Type BOTH
InChI Key PEASPLKKXBYDKL-FXEVSJAOSA-N
Therapeutic ✓ Yes

Known Names

DP-178 DP178 Enfuvirtida Enfuvirtide Fuzeon Fuzeon t-20 Pentafuside (trivial name) T-20 T20
4
Targets
107
Activities
3
Assay Types
13
PK Parameters
20
Publications
9
Known Names
4
Indications
1
Mechanisms

Molecular Properties

4491.9
MW (Da)

Drug Information

Molecule Type Protein
First Approval 2003
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

First in Class
USAN Stem -tide; -vir-
USAN Year 2001

Extended Properties

Molecular Formula C204H301N51O64
MW 4491.94

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Transmembrane glycoprotein gp41 inhibitor INHIBITOR Transmembrane glycoprotein gp41

Indications

HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome

ATC Classification

J05AX07
enfuvirtide
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

IC50 56 meas. best 8.8
EC50 50 meas. best 9.0
Kd 1 meas. best 6.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 9.0 7.6083 1.0 46
Human immunodeficiency virus 1
CHEMBL378
IC50 8.8 6.7347 1.6 55
GP41
CHEMBL3559676
EC50 8.0 7.3733 10.1 3
Unchecked
CHEMBL612545
IC50 8.0 8.0 10.0 1
GP41
CHEMBL3559676
Kd 6.74 6.74 182.0 1
Human immunodeficiency virus 2
CHEMBL380
EC50 6.44 6.44 360.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 26900.0 ng.hr.mL-1 Rattus norvegicus
CL 0.6667 mL.min-1.kg-1 Macaca fascicularis
Cmax 5676834.51 nM Rattus norvegicus
Ka - - Homo sapiens
MRT 2.1 hr Rattus norvegicus
T1/2 8.8 hr Macaca fascicularis
T1/2 2.8 hr Rattus norvegicus
T1/2 2.18 hr Rattus norvegicus
T1/2 0.516 hr Rattus norvegicus
T1/2 0.598 hr Rattus norvegicus
T1/2 0.905 hr -
T1/2 1.5 hr Rattus norvegicus
Vd 0.44 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 X4 in human PBMC assessed as reduction of p24 an... 17485501
Human immunodeficiency virus 1 EC50 = 1.58 nM 8.8 Anti-HIV-1 activity against HIV1 BaL (subtype B, R5) assessed as inhibition of i... 34261320
Human immunodeficiency virus 1 IC50 = 1.58 nM 8.8 Antiviral activity against HIV 1 BaL(R5) incubated overnight by ELISA analysis 33929200
Human immunodeficiency virus 1 EC50 = 2.4 nM 8.62 Antiviral activity against enfuvirtide-resistant Human immunodeficiency virus 1 ... 19114674
Human immunodeficiency virus 1 EC50 = 2.54 nM 8.6 Antiviral activity against HIV-1 clinical isolate 97 TH-NP1525 infected in human... 36944281
Human immunodeficiency virus 1 EC50 = 2.88 nM 8.54 Antiviral activity against HIV1 BaL infected in human MT2 cells assessed as inhi... 25156906
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV1 3B/LA1 infected in human CD4+ T-cell assessed as... 19805567
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV-1 SF33 infected in TZM-bl cells after 2 days by l... 25594223
Human immunodeficiency virus 1 IC50 = 3.0 nM 8.52 Antiviral activity against HIV1 X4 IIIB MN/H9 (84US_MNp) clinical isolate infect... 37706450
Human immunodeficiency virus 1 EC50 = 3.4 nM 8.47 Antiviral activity against enfuvirtide-resistant Human immunodeficiency virus 1 ... 19114674
Human immunodeficiency virus 1 EC50 = 3.6 nM 8.44 Antiviral activity against HIV1 NL4.3 in human PBMC assessed as p24 antigen leve... 19805567
Human immunodeficiency virus 1 EC50 = 4.02 nM 8.4 Antiviral activity against HIV-1 Bal-R5 infected in human CEMx174 5.25M7 cells a... 36944281
Human immunodeficiency virus 1 IC50 = 4.0 nM 8.4 Antiviral activity against HIV-1 group O 20547806
Human immunodeficiency virus 1 EC50 = 4.31 nM 8.37 Anti-HIV-1 activity against T20-sensitive HIV1 D36G assessed as inhibition of in... 34261320
Human immunodeficiency virus 1 EC50 = 6.3 nM 8.2 Antiviral activity against HIV1 US2 clade B, R5 in human PBMC assessed as p24 an... 19805567
Human immunodeficiency virus 1 IC50 = 6.4 nM 8.19 Antiviral activity against HIV-1 group O expressing gp41 N42D, N43K mutant gene 20547806
Human immunodeficiency virus 1 IC50 = 6.5 nM 8.19 Antiviral activity against HIV1 QA013.701.ENV.M12 clinical isolate infected in h... 37706450
Human immunodeficiency virus 1 IC50 = 6.4 nM 8.19 Antiviral activity against HIV-1 group M 20547806
Human immunodeficiency virus 1 EC50 = 7.55 nM 8.12 Antiviral activity against HIV-1 Ba-L subtype B infected in human PBMC assessed ... 24856833
Human immunodeficiency virus 1 IC50 = 7.86 nM 8.11 Antiviral activity against HIV 1 JRFL subtype B assessed as inhibition of viral ... 33929200

Literature References

PubMed DOI Target Context # Activities
26256053 10.1021/acs.jmedchem.5b00109 Human immunodeficiency virus 1 28
17954689 10.1128/aac.00737-07 Human immunodeficiency virus 1 22
19114674 10.1128/aac.01211-08 Human immunodeficiency virus 1 16
24856833 10.1021/jm500344y Human immunodeficiency virus 1 14
25156906 10.1021/jm500763m Human immunodeficiency virus 1 13
23673219 10.1016/j.bmc.2013.04.046 Human immunodeficiency virus 1 11
19805567 10.1128/aac.00827-09 Human immunodeficiency virus 1 10
19949052 10.1128/aac.00891-09 Human immunodeficiency virus 1 9
19124665 10.1128/aac.01067-08 Human immunodeficiency virus 1 8
17485501 10.1128/aac.01602-06 Human immunodeficiency virus 1 8
37706450 10.1021/acs.jmedchem.3c01412 Human immunodeficiency virus 1 7
36944281 10.1016/j.ejmech.2023.115294 Human immunodeficiency virus 1 6
24856833 10.1021/jm500344y ADMET 6
20547806 10.1128/aac.00100-10 Human immunodeficiency virus 1 5
33929200 10.1021/acs.jmedchem.1c00258 Human immunodeficiency virus 1 5
34261320 10.1021/acs.jmedchem.1c00781 Human immunodeficiency virus 1 5
25156906 10.1021/jm500763m Rattus norvegicus 5
17640899 10.1073/pnas.0701478104 Human immunodeficiency virus 1 5
23002902 10.1021/np300255r Human immunodeficiency virus 1 4
25156906 10.1021/jm500763m GP41 4

Data from ChEMBL 36 via Core Engine