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

Details

Stereochemistry MIXED
Molecular Formula C66H72N6O15PS.3HO
Molecular Weight 1303.37
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UKRAIN

SMILES

[OH-].[OH-].[OH-].[H][C@]12[C@@H](O)CC3=CC4=C(OCO4)C=C3[C@@]1([H])[N+](C)(CCNP(=S)(NCC[N+]5(C)CC6=C(C=CC7=C6OCO7)[C@@]8([H])[C@@H](O)CC9=CC%10=C(OCO%10)C=C9[C@@]58[H])NCC[N+]%11(C)CC%12=C(C=CC%13=C%12OCO%13)[C@@]%14([H])[C@@H](O)CC%15=CC%16=C(OCO%16)C=C%15[C@@]%11%14[H])CC%17=C2C=CC%18=C%17OCO%18

InChI

InChIKey=KIGCDEJCMKDBHU-NIQQUOCOSA-K
InChI=1S/C66H72N6O15PS.3H2O/c1-70(25-43-37(4-7-49-64(43)85-31-76-49)58-46(73)16-34-19-52-55(82-28-79-52)22-40(34)61(58)70)13-10-67-88(89,68-11-14-71(2)26-44-38(5-8-50-65(44)86-32-77-50)59-47(74)17-35-20-53-56(83-29-80-53)23-41(35)62(59)71)69-12-15-72(3)27-45-39(6-9-51-66(45)87-33-78-51)60-48(75)18-36-21-54-57(84-30-81-54)24-42(36)63(60)72;;;/h4-9,19-24,46-48,58-63,73-75H,10-18,25-33H2,1-3H3,(H3,67,68,69,89);3*1H2/q+3;;;/p-3/t46-,47-,48-,58-,59-,60-,61+,62+,63+,70?,71?,72?,88?;;;/m0.../s1

HIDE SMILES / InChI
NSC-631570 (Ukrain) is a semisynthetic compound of thiophosphoric acid and the alkaloid chelidonine from the plant Chelidonium majus. Ukrain was promoted as a drug to treat cancer and viral infections, including HIV and hepatitis. It exerts a selective cytotoxic effect on tumor cells in vitro and in vivo and shows the ability to modulate immunocyte functions. Ukrain has been used in complementary herbal medicine for more than 20 years for the treatment of benign and malignant tumors. Thus, in unresectable advanced pancreatic cancer, Ukrain alone and in combination with gemcitabine nearly doubled the median survival times in patients suffering from advanced pancreatic cancer. Inhibition of the growth of cancer cell lines in vitro, tumor mass reductions in vivo, and partial and complete remissions in oncological patients, occur as a result of Ukrain application. The drug may interfere directly with the metabolism of cancer cells and it also improves the functioning of the host immune system. Diminished synthesis of DNA, RNA and proteins, the inhibition of cellular oxygen consumption, and the induction of programmed cell death in malignant cells have been described following Ukrain administration. The drug can also modify the immunological response via an increase in the number of total T-cells and a normalization of the T-helper/T-suppressor lymphocyte ratio. However,according to the American Cancer Society and the Memorial Sloan-Kettering Cancer Center, there is no evidence that Ukrain is an effective cancer treatment. Through an Austrian company known as Nowicky Pharma, the drug, which was never approved by regulators, was sold as a treatment for AIDS, radiation-induced diseases and as a cure for all forms of cancer. Ukrain is not approved by the Food and Drug Administration but is available in parts of Europe and from Tijuana clinics.

Approval Year

PubMed

PubMed

TitleDatePubMed
Modulation of immune effector cell cytolytic activity and tumour growth inhibition in vivo by Ukrain (NSC 631570).
1996
NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial.
2002 Mar
Patents

Patents

Sample Use Guides

Breast cancer: 5 mg every second day for 20 days
Route of Administration: Intravenous
In Vitro Use Guide
Pretreatment of PEM (peritoneal exudate macrophages) from normal mice with 2.5 uM Ukrain for 24 h, followed by stimulation with either IFN-gamma or with lipopolysaccharide (LPS) plus IFN-gamma enhanced their cytotoxic activity. Treatment of PEM from tumour-bearing mice with 2.5 uM Ukrain and LPS results in a reversal of their defective cytotoxic response against DA-3 target cells.
Name Type Language
UKRAIN
Common Name English
NSC-631570
Code English
CHELIDONINIUM, 5,5',5''-(PHOSPHINOTHIOYLIDYNETRIS(IMINO-2,1-ETHANEDIYL))TRIS(5-METHYL-, TRIHYDROXIDE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 169303
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID2043955
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
NSC
631570
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
SMS_ID
100000144485
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
PUBCHEM
160027
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
EVMPD
SUB121117
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
CAS
138069-52-0
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
WIKIPEDIA
Ukrain
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
FDA UNII
6251Q9UK1S
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY
MESH
C060921
Created by admin on Sat Dec 16 01:57:23 GMT 2023 , Edited by admin on Sat Dec 16 01:57:23 GMT 2023
PRIMARY