Cycloguanil HCl | CAS#152-53-4 | 609-78-9 | Antimalarial Drug

MedKoo Cat#: 524922 | Name: Cycloguanil HCl

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cycloguanil is a dihydrofolate reductase inhibitor, and is a metabolite of the antimalarial drug proguanil; its formation in vivo has been thought to be primarily responsible for the antimalarial activity of proguanil. However, more recent work has indicated that, while proguanil is synergistic with the drug atovaquone (as in the combination Malarone), cycloguanil is in fact antagonistic to the effects of atovaquone, suggesting that, unlike cycloguanil, proguanil may have an alternative mechanism of antimalarial action besides dihydrofolate reductase inhibition.

Chemical Structure

Cycloguanil HCl

CAS#152-53-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 524922

Name: Cycloguanil HCl

CAS#: 152-53-4 (HCl)

Chemical Formula: C11H15Cl2N5

Exact Mass: 0.0000

Molecular Weight: 288.18

Elemental Analysis: C, 45.85; H, 5.25; Cl, 24.60; N, 24.30

Price and Availability

Size	Price	Availability
100mg	USD 300.00	2 Weeks
250mg	USD 550.00	2 Weeks
500mg	USD 850.00	2 Weeks
1g	USD 1,250.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

152-53-4 (HCl) 516-21-2 (free base) 25332-44-9 (nitrate) 609-78-9 (pamoate)

Synonym

NSC 3074; NSC-3074; NSC3074; Cycloguanil HCl; Cycloguanil hydrochloride, Chloroguanide Triazine HCl

IUPAC/Chemical Name

1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine hydrochloride

InChi Key

MOUAPRKJJUXEIE-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H14ClN5.ClH/c1-11(2)16-9(13)15-10(14)17(11)8-5-3-7(12)4-6-8;/h3-6H,1-2H3,(H4,13,14,15,16);1H

SMILES Code

NC1=NC(N)=NC(C)(C)N1C2=CC=C(Cl)C=C2.[H]Cl

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 288.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Le Bras J, Basco LK, Cremer G, Charmot G. [Contribution of molecular genetics to the understanding of chemoresistance of Plasmodium falciparum]. Bull Soc Pathol Exot. 1992;85(2):146-9. Review. French. PubMed PMID: 1356539. 2: Schmidt LH, Rossan RN. Activities of respository preparations of cycloguanil pamoate and 4,4'-diacetyldiaminodiphenylsulfone, alone and in combination, against infections with Plasmodium cynomolgi in rhesus monkeys. Antimicrob Agents Chemother. 1984 Nov;26(5):611-42. PubMed PMID: 6393864; PubMed Central PMCID: PMC179984. 3: Werbel LM, Jacobs RL, Steinkampf RW, Worth DF. Long-acting, repository antimalarial agents. Duration of protection in mice and monkeys following administration of pyrimethamine pamoate. Am J Trop Med Hyg. 1984 Jul;33(4):526-33. PubMed PMID: 6236702. 4: Mrema JE, Rieckmann KH. A rabbit--in vitro system to evaluate drug action against Plasmodium falciparum. Trans R Soc Trop Med Hyg. 1983;77(1):130-5. PubMed PMID: 6222522. 5: Ardehali M. Treatment of cutaneous leishmaniasis with cycloguanil pamoate. Int J Dermatol. 1974 Jan-Feb;13(1):26-8. PubMed PMID: 4813519. 6: Harwin RM. A field trial of the effectiveness of cycloguanil pamoate in Rhodesia. Cent Afr J Med. 1973 Jan;19(1):9-12. PubMed PMID: 4576484. 7: Lowenthal MN, O'Riordan EC, Hutt MS. Tropical splenomegaly syndrome in Zambia: further observations and effects of cycloguanil and proguanil. Br Med J. 1971 Feb 20;1(5746):429-32. PubMed PMID: 5101344; PubMed Central PMCID: PMC1795042. 8: Reinhard M, Wacker H. [Therapy of cutaneous leishmaniasis (Leishmania tropica) with cycloguanil pamoate]. Dtsch Med Wochenschr. 1970 Nov 20;95(47):2380-2. German. PubMed PMID: 5481970. 9: Fasan PO. Field trial of cycloguanil pamoate in the treatment and suppression of malaria in Nigerian school children: a preliminary report. Trans R Soc Trop Med Hyg. 1970;64(6):839-49. PubMed PMID: 5495634. 10: Salem HH, Elkomy HM, el-Allaf G. The treatment of cutaneous leishmaniasis in Iraq with cycloguanil pamoate. Trans R Soc Trop Med Hyg. 1969;63(3):388-92. PubMed PMID: 5795162. 11: Johnson CM. Cycloguanil pamoate in the treatment of cutaneous leishmaniasis. Initial trials in Panamá. Am J Trop Med Hyg. 1968 Nov;17(6):819-22. PubMed PMID: 5726132. 12: Walton BC, Person DA, Ellman MH, Bernstein R. Treatment of American cutaneous leishmaniasis with cycloguanil pamoate. Am J Trop Med Hyg. 1968 Nov;17(6):814-7. PubMed PMID: 4302275. 13: Pena Chavarria A, Kotcher E, Lizano C. Treatment of American dermal leishmaniasis with cycloguanil pamoate. Trans R Soc Trop Med Hyg. 1968;62(4):550-5. PubMed PMID: 5671542. 14: Chin W, Contacos PG, Coatney GR, Jeter MH, Alpert E. Evaluation of CI-564, A 1:1 mixture of cycloguanil pamoate (CI-501) and 4,4'-diacetylaminodiphenylsulfone (CI-556), against multiresistant falciparum malarias. Am J Trop Med Hyg. 1967 Sep;16(5):580-4. PubMed PMID: 4861322. 15: Laing AB, Pringle G, Lane FC. A study among African school-children of the repository antimalarial properties of cycloguanil pamoate, 4,4+-diacetyldiaminodiphenylsulfone, and a combination of the two drugs. Am J Trop Med Hyg. 1966 Nov;15(6):838-48. PubMed PMID: 5335427. 16: Rieckmann KH. A field study on the effects of a combination of cycloguanil pamoate and amodiquine against malaria in the Rabaul area of New Guinea. Am J Trop Med Hyg. 1966 Nov;15(6):833-7. PubMed PMID: 5335161. 17: Contacos PG, Coatney GR, Lunn JS, Chin W. The urinary excretion and the antimalarial activity of CI-501 (cycloguanil-pamoate, Camolar) against vivax and falciparum malaria. Am J Trop Med Hyg. 1966 May;15(3):281-6. PubMed PMID: 5328125. 18: McGregor IA, Williams K, Walker GH, Rahman AK. Cycloguanil pamoate in the treatment and suppression of malaria in the Gambia, West Africa. Br Med J. 1966 Mar 19;1(5489):695-701. PubMed PMID: 5909480; PubMed Central PMCID: PMC1844242. 19: Peña Chavarría A, Kotcher E, Lizano C. Preliminary evaluation of cycloguanil pamoate in dermal leishmaniasis. JAMA. 1965 Dec 6;194(10):1142-4. PubMed PMID: 5897797. 20: Contacos PG, Coatney GR, Lunn JS, Chin W. Resistance to cycloguanil pamoate (CI-501) by falciparum malaria in West Pakistan. Am J Trop Med Hyg. 1965 Nov;14(6):925-6. PubMed PMID: 5320456.