Pafolacianine sodiumProduct ingredient for Pafolacianine

Name
Pafolacianine sodium
Drug Entry
Pafolacianine

Pafolacianine, or OTL38, is a folate analogue conjugated with a fluorescent dye that absorbs light in the near-infrared (NIR) spectrum 3 within a range of 760 nm to 785 nm, with a peak absorption of 776 nm. It emits fluorescence within a range of 790 nm to 815 nm with a peak emission of 796 nm.5 The longer wavelength allows for deeper penetration of the fluorescent light through tissues for better imaging and detection of tumours. Pafolacianine targets the folate receptor alpha (FRα) which is upregulated in numerous epithelial malignancies.3

On November 29, 2021, the FDA approved pafolacianine as an adjunct imaging agent for intraoperative identification of malignant lesions in adult patients with ovarian cancer.5 It is currently under investigation for use in FRα-positive pituitary adenoma, lung cancer,4 and renal-cell carcinoma, which is thought to be the second-highest folate receptor-expressing cancer.3

Accession Number
DBSALT003214
Structure
Synonyms
Pafolacianine sodium / Pafolacianine tetrasodium
UNII
4HUF3V875C
CAS Number
1628858-03-6
Weight
Average: 1414.42
Monoisotopic: 1413.28155342
Chemical Formula
C61H63N9Na4O17S4
InChI Key
LRVBSDMJFVZFHH-NFVAJSDSSA-J
InChI
InChI=1S/C61H67N9O17S4.4Na/c1-60(2)46-33-44(90(81,82)83)22-24-49(46)69(28-5-7-30-88(75,76)77)51(60)26-16-38-10-9-11-39(17-27-52-61(3,4)47-34-45(91(84,85)86)23-25-50(47)70(52)29-6-8-31-89(78,79)80)54(38)87-43-20-12-37(13-21-43)32-48(58(73)74)66-56(71)40-14-18-41(19-15-40)63-35-42-36-64-55-53(65-42)57(72)68-59(62)67-55;;;;/h12-27,33-34,36,48H,5-11,28-32,35H2,1-4H3,(H9-,62,63,64,66,67,68,71,72,73,74,75,76,77,78,79,80,81,82,83,84,85,86);;;;/q;4*+1/p-4/t48-;;;;/m0..../s1
IUPAC Name
tetrasodium 2-[(1E)-2-[(3E)-2-{4-[(2S)-2-[(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-2-carboxylatoethyl]phenoxy}-3-{2-[(2Z)-3,3-dimethyl-5-sulfonato-1-(4-sulfonatobutyl)-2,3-dihydro-1H-indol-2-ylidene]ethylidene}cyclohex-1-en-1-yl]ethenyl]-3,3-dimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium-5-sulfonate
SMILES
[Na+].[Na+].[Na+].[Na+].CC1(C)C(=C\C=C2/CCCC(\C=C\C3=[N+](CCCCS([O-])(=O)=O)C4=C(C=C(C=C4)S([O-])(=O)=O)C3(C)C)=C2OC2=CC=C(C[C@H](NC(=O)C3=CC=C(NCC4=NC5=C(N=C4)N=C(N)NC5=O)C=C3)C([O-])=O)C=C2)N(CCCCS([O-])(=O)=O)C2=C1C=C(C=C2)S([O-])(=O)=O
ChEMBL
CHEMBL4594383
Predicted Properties
PropertyValueSource
Water Solubility0.00107 mg/mLALOGPS
logP2.41ALOGPS
logP2.26Chemaxon
logS-6.1ALOGPS
pKa (Strongest Acidic)-2.2Chemaxon
pKa (Strongest Basic)2.12Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count23Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area418.8 Å2Chemaxon
Rotatable Bond Count25Chemaxon
Refractivity362.55 m3·mol-1Chemaxon
Polarizability135.73 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon