C9419
4-Chloro-D-phenylalanine
Synonym(s):
D-PCP, D-PCPA
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About This Item
Empirical Formula (Hill Notation):
C9H10ClNO2
CAS Number:
Molecular Weight:
199.63
Beilstein:
2416151
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
form
solid
technique(s)
ligand binding assay: suitable
storage temp.
−20°C
SMILES string
N[C@H](Cc1ccc(Cl)cc1)C(O)=O
InChI
1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1
InChI key
NIGWMJHCCYYCSF-MRVPVSSYSA-N
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Biochem/physiol Actions
4-Chloro-D-phenylalanine (D-PCP, D-Phe(4Cl)) is a component of the synthetic decapeptide SB-4-Chloro-D-phenylalanine. (D-PCP, D-Phe(4Cl)) is a component of the synthetic peptides SB-75/cetrorelix, a Gonadotropin Releasing Hormone (GnRH) antagonist, and of the VIP receptor antagonist (4Cl-D-Phe(6),Leu(17))-VIP.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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J Pinski et al.
International journal of peptide and protein research, 45(5), 410-417 (1995-05-01)
The objective of this study was to examine the in vivo and in vitro gonadotropin-inhibiting potencies, edematogenic activities and the receptor binding affinities of the D-Cit6, D,L-Cit6 and L-Cit6 forms of the LH-RH antagonist Cetrorelix (SB-75) [Ac-D-Nal(2)1,D-Phe(4Cl)2,D-Pal(3)3,D-Cit6,D-Ala10]LH- RH. In order
S Kordasti et al.
Gut, 53(7), 952-957 (2004-06-15)
The mechanisms underlying intestinal secretion in rotavirus diarrhoea remain to be established. We previously reported that rotavirus evokes intestinal fluid and electrolyte secretion by activation of the enteric nervous system. We now report that antagonists for the 5-hydroxytryptamine 3 receptor
J Horvath et al.
International journal of oncology, 6(5), 969-975 (1995-05-01)
The effects of luteinizing hormone-releasing hormone (LH-RH), and LH-RH antagonist Cetrorelix, (SB-75, [Ac-D-Nal(2)(1),D-Phe(4-Cl)(2),D-Pal(3)(3),D-Cit(6),D-Ala(10)]LH-RH) on cell growth and the production of hCG and cAMP in JAR human choriocarcinoma cells were examined in vitro. Both LH-RH and its antagonist SE-75, at 1
T Yano et al.
Proceedings of the National Academy of Sciences of the United States of America, 91(15), 7090-7094 (1994-07-19)
Female athymic nude mice bearing xenografts of OV-1063 human epithelial ovarian cancer cell line were treated with potent luteinizing hormone (LH)-releasing hormone (LH-RH) antagonist SB-75 (Cetrorelix; [Ac-D-Nal(2)1, D-Phe(4 CI)2, D-Pal(3)3, D-Cit6, D-Ala10]LH-RH in which Ac-D-Nal(2) = N-acetyl-3-(2-naphthyl)-D-alanine, D-Phe(4CI) = 4-chloro-D-phenylalanine
Takeharu Niioka et al.
Archives of oral biology, 54(10), 909-916 (2009-08-04)
The parasympathetic vasodilatory fibres are known to innervate vessels in a rat masseter muscle via both cholinergic and non-cholinergic mechanisms. However, the non-cholinergic mechanisms are still unclear. Recently, vasoactive intestinal polypeptide (VIP) was convincingly shown to be involved in the
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