Azetidine-3-carboxylic acid

Names

[ Name ]:
Azetidine-3-carboxylic acid

[Synonym ]:
Azetidine-3-carboxylic Acid
3-Azetidinecarboxylic acid
MFCD00191763
3-Azetidine carboxylic acid

Biological Activity

[Description]:

Azetidine-3-carboxylic acid is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). Azetidine-3-carboxylic acid is also a alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs[1][2

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Antibody-drug Conjugate >> ADC Linker

Signaling Pathways >> PROTAC >> PROTAC Linker

[Target]

Non-cleavable

[In Vitro]

ADCs are comprised of an antibody to which is attached an ADC cytotoxin through an ADC linker[1]. PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins[2].

[References]

[1]. Beck A, et al. Strategies and challenges for the next generation of antibody-drug conjugates. Nat Rev Drug Discov. 2017;16(5):315-337.

[2]. Nalawansha DA, et al. PROTACs: An Emerging Therapeutic Modality in Precision Medicine. Cell Chem Biol. 2020;27(8):998-985.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
242.0±33.0 °C at 760 mmHg

[ Melting Point ]:
286 °C (dec.)(lit.)

[ Molecular Formula ]:
C₄H₇NO₂

[ Molecular Weight ]:
101.104

[ Flash Point ]:
100.1±25.4 °C

[ Exact Mass ]:
101.047676

[ PSA ]:
49.33000

[ LogP ]:
-0.86

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.499

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CM4310600

CHEMICAL NAME :: 3-Azetidinecarboxylic acid

CAS REGISTRY NUMBER :: 36476-78-5

BEILSTEIN REFERENCE NO. :: 0385928

LAST UPDATED :: 199710

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C4-H7-N-O2

MOLECULAR WEIGHT :: 101.12

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C65,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C65,1991

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25-S22

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CM4310600

[ HS Code ]:
2933990090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Beta-proline analogues as agonists at the strychnine-sensitive glycine receptor.

J. Med. Chem. 35 , 233, (1992)

3-Carboxy-3,4-dehydropyrrolidine was found to bind with affinity equal to that of glycine in a [3H]strychnine binding assay. Simple substitution of the 1-, 2-, 4-, or 5-position resulted in marked los...

Weed Sci. 38 , 315, (1990)

Related Compounds

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