U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H17N3O2S
Molecular Weight 243.326
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-IMINOBIOTIN

SMILES

[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=N)N2

InChI

InChIKey=WWVANQJRLPIHNS-ZKWXMUAHSA-N
InChI=1S/C10H17N3O2S/c11-10-12-6-5-16-7(9(6)13-10)3-1-2-4-8(14)15/h6-7,9H,1-5H2,(H,14,15)(H3,11,12,13)/t6-,7-,9-/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H17N3O2S
Molecular Weight 243.326
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02836340 | https://www.ncbi.nlm.nih.gov/pubmed/27780726 | https://clinicaltrials.gov/ct2/show/NCT01626924

2-Iminobiotin (2-IB) is a cyclic guanidino analog of biotin (Vitamin B7) and combined neuronal and inducible (but not endothelial) nitric oxide synthase inhibitor that has been demonstrated to improve neuroprotection in animal models of hypoxic-ischemic Brain Injury. While the exact mechanism of action has yet to be defined, 2-Iminobiotin potentially protects against hypoxic-ischemic brain damage by preventing nitric oxide or peroxynitrite-induced mitochondrial damage. In preclinical models, 2-Iminobiotin provides gender-specific neuroprotection against hypoxia-ischemia in neonatal rats by a NO-independent mechanism.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
21.8 nM [Ki]
37.5 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
22541 ng/mL
6 mg/kg 6 times / day multiple, intravenous
dose: 6 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
34175 ng/mL
12 mg/kg 6 times / day multiple, intravenous
dose: 12 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1808 ng/mL
0.6 mg/kg single, intravenous
dose: 0.6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
16448 ng × h/mL
6 mg/kg 6 times / day multiple, intravenous
dose: 6 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
39956 ng × h/mL
12 mg/kg 6 times / day multiple, intravenous
dose: 12 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1528 ng × h/mL
0.6 mg/kg single, intravenous
dose: 0.6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.12 h
6 mg/kg 6 times / day multiple, intravenous
dose: 6 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.37 h
12 mg/kg 6 times / day multiple, intravenous
dose: 12 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.48 h
0.6 mg/kg single, intravenous
dose: 0.6 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
2-IMINOBIOTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
12 mg/kg 6 times / day multiple, intravenous
Highest studied dose
Dose: 12 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
Disc. AE: Dizziness, Headache...
AEs leading to
discontinuation/dose reduction:
Dizziness (grade 1-2, 33.3%)
Headache (grade 1, 16.7%)
Pallor of skin (grade 1, 16.7%)
Malaise (grade 2, 16.7%)
Abdominal pain (grade 1, 16.7%)
Nausea (grade 2, 33.3%)
Sources: Page: p.155
6 mg/kg 6 times / day multiple, intravenous
MTD
Dose: 6 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 6 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
AEs

AEs

AESignificanceDosePopulation
Abdominal pain grade 1, 16.7%
Disc. AE
12 mg/kg 6 times / day multiple, intravenous
Highest studied dose
Dose: 12 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
Headache grade 1, 16.7%
Disc. AE
12 mg/kg 6 times / day multiple, intravenous
Highest studied dose
Dose: 12 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
Pallor of skin grade 1, 16.7%
Disc. AE
12 mg/kg 6 times / day multiple, intravenous
Highest studied dose
Dose: 12 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
Dizziness grade 1-2, 33.3%
Disc. AE
12 mg/kg 6 times / day multiple, intravenous
Highest studied dose
Dose: 12 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
Malaise grade 2, 16.7%
Disc. AE
12 mg/kg 6 times / day multiple, intravenous
Highest studied dose
Dose: 12 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
Nausea grade 2, 33.3%
Disc. AE
12 mg/kg 6 times / day multiple, intravenous
Highest studied dose
Dose: 12 mg/kg, 6 times / day
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 6 times / day
Sources: Page: p.155
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.155
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Short-term dose-response characteristics of 2-iminobiotin immediately postinsult in the neonatal piglet after hypoxia-ischemia.
2013 Mar
Patents

Patents

Sample Use Guides

2-Iminobiotin is formulated as a 0.75 mg/ml isotonic, iso-osmotic, saline solution with a pH of 4. It is administered as a solution for I.V.infusion through a central catheter. Six pulse doses will be given in 20 hours. Dosage will starts with 0.2 mg/kg/dose, but may be adapted during the study.
Route of Administration: Intravenous
Neuronal IMR-32 cells were exposed to hypoxia employing an enzymatic hypoxia system and were thereafter incubated with various concentrations of 2-IB (10 to 300ng/ml). Cell damage, metabolic activity and generation of reactive oxygen species were quantified using colorimetric/fluorometric lactate dehydrogenase (LDH), tetrazolium-based (MTS) and reactive oxygen species assays. Proteome profiling arrays were performed to evaluate the regulation of cell stress protein expression by hypoxia and 2-IB. Seven hours of hypoxia led to morphological changes in IMR-32 cultures, increased neuronal cell damage, reduction of metabolic activity and enhanced reactive oxygen species production. Post-hypoxic application of 2-IB (30ng/ml) attenuated hypoxia-induced LDH release and increased metabolic activity of IMR-32 cells, while reactive oxygen species production was only by trend decreased.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:17:39 GMT 2023
Edited
by admin
on Sat Dec 16 05:17:39 GMT 2023
Record UNII
HXH71NRQ5C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-IMINOBIOTIN
Common Name English
1H-THIENO(3,4-D)IMIDAZOLE-4-PENTANOIC ACID, 2-AMINO-3A,4,6,6A-TETRAHYDRO-, (3AS,4S,6AR)-
Common Name English
HEXAHYDRO-2-IMINO-1H-THIENO(3,4-D)IMIDAZOLE-4-PENTANOIC ACID
Systematic Name English
1H-THIENO(3,4-D)IMIDAZOLE-6-PENTANOIC ACID, 2-AMINO-3A,4,6,6A-TETRAHYDRO-, (3AR,6S,6AS)-
Common Name English
THIENO(3,4-D)IMIDAZOLINE-4-VALERIC ACID, TETRAHYDRO-2-IMINO-
Common Name English
5-((3AS,4S,6AR)-2-IMINOHEXAHYDRO-1H-THIENO(3,4-D)IMIDAZOL-4-YL)PENTANOIC ACID
Common Name English
GUANIDINOBIOTIN
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 275609
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
EU-Orphan Drug EU/3/09/701
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
Code System Code Type Description
PUBCHEM
128878
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID20158431
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
PRIMARY
FDA UNII
HXH71NRQ5C
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
PRIMARY
SMS_ID
100000178201
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
PRIMARY
CAS
13395-35-2
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
PRIMARY
DRUG BANK
DB03353
Created by admin on Sat Dec 16 05:17:39 GMT 2023 , Edited by admin on Sat Dec 16 05:17:39 GMT 2023
PRIMARY