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

Details

Stereochemistry ABSOLUTE
Molecular Formula C4H6N4O3
Molecular Weight 158.1154
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALLANTOIN, (+)-

SMILES

NC(=O)N[C@H]1NC(=O)NC1=O

InChI

InChIKey=POJWUDADGALRAB-SFOWXEAESA-N
InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)/t1-/m0/s1

HIDE SMILES / InChI

Molecular Formula C4H6N4O3
Molecular Weight 158.1154
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.akema.it/pdf/allantoin_ctfa.pdf | http://adisinsight.springer.com/drugs/800037582 | https://www.ncbi.nlm.nih.gov/pubmed/16485000 | https://www.ncbi.nlm.nih.gov/pubmed/16462750

Allantoin is a metabolic intermediate of a wide variety of organims: from bacteria to vegetals and animals. Allantoin is a skin active ingridient with keratolytic, moisturizing, anti-irritant properties, promotes renewal of epidermal cell and accelerates wounds healing. Allantoin possesses one chiral center thereby exists in the two enantiomeric forms R-(-) and S-( ). Enzymes that catalyze the formation of (S)-allantoin from the product of the urate oxidase reaction have been identified. The two proteins encoded by mouse genes catalyze two consecutive steps following urate oxidation to 5-hydroxyisourate (HIU): hydrolysis of HIU to give 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline (OHCU) and decarboxylation of OHCU to give S-( )-allantoin. Urate oxidation produces racemic allantoin on a time scale of hours, whereas the full enzymatic complement produces dextrorotatory allantoin on a time scale of seconds. Scioderm is developing Allantoin (Zorblisa; SD-101), as a novel topical therapy for patients with epidermolysis bullosa.

CNS Activity

Curator's Comment: No human data available.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: UniProtKB - E3SAZ9 (Allantoin racemase)
Target ID: P32375
Gene ID: 854845.0
Gene Symbol: DAL1
Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)
Conditions
Doses

Doses

DosePopulationAdverse events​
6 % 1 times / day multiple, topical (unknown)
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
n = 82
Health Status: unhealthy
Condition: epidermolysis bullosa
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 82
Sources:
Other AEs: Pruritus, Urticaria...
Other AEs:
Pruritus (7.3%)
Urticaria (2.4%)
Dry skin (2.4%)
Blister (2.4%)
wound (2.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Blister 2.4%
6 % 1 times / day multiple, topical (unknown)
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
n = 82
Health Status: unhealthy
Condition: epidermolysis bullosa
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 82
Sources:
Dry skin 2.4%
6 % 1 times / day multiple, topical (unknown)
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
n = 82
Health Status: unhealthy
Condition: epidermolysis bullosa
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 82
Sources:
Urticaria 2.4%
6 % 1 times / day multiple, topical (unknown)
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
n = 82
Health Status: unhealthy
Condition: epidermolysis bullosa
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 82
Sources:
wound 2.4%
6 % 1 times / day multiple, topical (unknown)
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
n = 82
Health Status: unhealthy
Condition: epidermolysis bullosa
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 82
Sources:
Pruritus 7.3%
6 % 1 times / day multiple, topical (unknown)
Studied dose
Dose: 6 %, 1 times / day
Route: topical
Route: multiple
Dose: 6 %, 1 times / day
Sources:
unhealthy, ADULT
n = 82
Health Status: unhealthy
Condition: epidermolysis bullosa
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 82
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Urate to allantoin, specifically (S)-allantoin.
2006 Mar
Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: comparison of computed and measured electronic circular dichroism spectra.
2009 Jun
Characterization of the structure and function of Klebsiella pneumoniae allantoin racemase.
2011 Jul 15
Reaction Mechanism and Catalytic Fingerprint of Allantoin Racemase.
2014 Jul 10
The Structure and Function of a Microbial Allantoin Racemase Reveal the Origin and Conservation of a Catalytic Mechanism.
2016 Nov 22
Patents

Sample Use Guides

In phase 3 trials, Allantoin (Zorblisa; SD-101) was applied topically, once a day to the entire body for 90 days.The typical use of allantoin is between 0.1-0.5% but may be increased up to 2%.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:00:38 GMT 2023
Edited
by admin
on Sat Dec 16 11:00:38 GMT 2023
Record UNII
XDK458E1J9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALLANTOIN, (+)-
Common Name English
ALLANTOIN, S-(+)-
Common Name English
UREA, N-((4S)-2,5-DIOXO-4-IMIDAZOLIDINYL)-
Systematic Name English
ALLANTOIN S-(+)-FORM [MI]
Common Name English
(+)-ALLANTOIN
Common Name English
S-(+)-ALLANTOIN
Common Name English
Code System Code Type Description
DAILYMED
XDK458E1J9
Created by admin on Sat Dec 16 11:00:38 GMT 2023 , Edited by admin on Sat Dec 16 11:00:38 GMT 2023
PRIMARY
MERCK INDEX
m1520
Created by admin on Sat Dec 16 11:00:38 GMT 2023 , Edited by admin on Sat Dec 16 11:00:38 GMT 2023
PRIMARY Merck Index
CAS
3844-67-5
Created by admin on Sat Dec 16 11:00:38 GMT 2023 , Edited by admin on Sat Dec 16 11:00:38 GMT 2023
PRIMARY
PUBCHEM
439714
Created by admin on Sat Dec 16 11:00:38 GMT 2023 , Edited by admin on Sat Dec 16 11:00:38 GMT 2023
PRIMARY
FDA UNII
XDK458E1J9
Created by admin on Sat Dec 16 11:00:38 GMT 2023 , Edited by admin on Sat Dec 16 11:00:38 GMT 2023
PRIMARY
RXCUI
1739978
Created by admin on Sat Dec 16 11:00:38 GMT 2023 , Edited by admin on Sat Dec 16 11:00:38 GMT 2023
PRIMARY