Details of the Drug

General Information of Drug (ID: DM2WE5K)

Drug Name

Ceruletide

Synonyms

Caerulein; Cerulein; Ceruletida; Ceruletidum; Ceruletida [INN-Spanish]; Ceruletidum [INN-Latin]; Ceruletide (USAN/INN); Ceruletide [USAN:INN:BAN]; 5-Oxo-L-prolyl-L-glutaminyl-L-alpha-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide; 5-Oxo-L-prolyl-L-glutaminyl-L-aspartyl-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamide 4-(hydrogen sulfate) (ester); 5-oxo-L-prolyl-L-glutaminyl-L-a-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-a-aspartyl-L-phenylalaninamide

Indication

Disease Entry	ICD 11	Status	REF
Caerulein stimulated gastric and pancreatic secretion	5A4Y	Approved	[1]
Solid tumour/cancer	2A00-2F9Z	Phase 3	[2]
------------------------------------------------------------------------------------

Therapeutic Class

Diagnostic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

1352.4

Logarithm of the Partition Coefficient (xlogp)

-3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is absorbed following intravenous administration []

Chemical Identifiers

Formula: C58H73N13O21S2
IUPAC Name: (3S)-3-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid
Canonical SMILES: C[C@H]([C@@H](C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]5CCC(=O)N5)O
InChI: InChI=1S/C58H73N13O21S2/c1-29(72)49(71-57(87)40(23-31-12-14-33(15-13-31)92-94(89,90)91)68-56(86)43(26-48(78)79)69-52(82)37(16-18-44(59)73)65-51(81)36-17-19-45(74)63-36)58(88)62-28-46(75)64-41(24-32-27-61-35-11-7-6-10-34(32)35)54(84)66-38(20-21-93-2)53(83)70-42(25-47(76)77)55(85)67-39(50(60)80)22-30-8-4-3-5-9-30/h3-15,27,29,36-43,49,61,72H,16-26,28H2,1-2H3,(H2,59,73)(H2,60,80)(H,62,88)(H,63,74)(H,64,75)(H,65,81)(H,66,84)(H,67,85)(H,68,86)(H,69,82)(H,70,83)(H,71,87)(H,76,77)(H,78,79)(H,89,90,91)/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49+/m1/s1
InChIKey: YRALAIOMGQZKOW-HYAOXDFASA-N

Cross-matching ID

PubChem CID: 16129675
ChEBI ID: CHEBI:59219
CAS Number: 17650-98-5
DrugBank ID: DB00403
TTD ID: D0Y9TS

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Gastrin/cholecystokinin type B receptor (CCKBR)	TTVFO0U	GASR_HUMAN	Agonist	[3]

------------------------------------------------------------------------------------

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Collagen alpha-1(I) chain (COL1A1)	OTI31178	CO1A1_HUMAN	Gene/Protein Processing	[4]
Intercellular adhesion molecule 1 (ICAM1)	OTTOIX77	ICAM1_HUMAN	Gene/Protein Processing	[4]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Gene/Protein Processing	[4]
Parathyroid hormone-related protein (PTHLH)	OTI1JF13	PTHR_HUMAN	Gene/Protein Processing	[4]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Caerulein stimulated gastric and pancreatic secretion

ICD Disease Classification

5A4Y

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Gastrin/cholecystokinin type B receptor (CCKBR)	DTT	CCKBR	6.53E-01	1.00E-03	4.05E-03

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7589).
3	Comparison of postprandial and ceruletide serum bile acid stimulation in dogs. J Vet Intern Med. 2008 Jul-Aug;22(4):873-8.
4	Acinar cell-specific knockout of the PTHrP gene decreases the proinflammatory and profibrotic responses in pancreatitis. Am J Physiol Gastrointest Liver Physiol. 2014 Sep 1;307(5):G533-49. doi: 10.1152/ajpgi.00428.2013. Epub 2014 Jul 17.